Tag: M.W=100-200

Reference of 630-17-1, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 630-17-1 as follows.

(0317) Obtained according to the general method described previously. (0318) Reagents: 3-(2,6-Difluorophenyl)-8-methyl-4-oxo-2-thioxo-1,2,3,4-tetrahydroquinazoline (0.32 mmol, 0.097 g), neopentyl bromide (0.64 mmol, 0.080 mL), K2CO3 (0.0045 g). (0319) The reaction conditions were: 12 hours at ambient temperature. (0320) Purification was carried out by means of silica gel column chromatography (hexane/ethyl acetate, in a ratio of 6:1 by volume). (0321) The yield obtained was: a white solid (51 mg, 42%). P.f.: 152.3 C. 1H-RMN (400 MHz, DMSO) delta: 7.94 (dd, 1H, J=7.9, 0.8 Hz), 7.81-7.73 (m, 2H), 7.49-7.40 (m, 3H), 3.34 (s, 2H), 2.60 (s, 3H), 0.95 (s, 9H). 13C-RMN (100 MHz, DMSO) delta: 160.7, 158.8 (d, 2C, J=252.2 Hz), 156.0, 145.9, 136.9, 135.1, 134.1, 126.9, 125.1, 118.8, 113.5, 44.9, 32.6, 28.9, 17.6, purity analysed by HPLC >99%. EM (m/z): 375 [M+H

According to the analysis of related databases, 630-17-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Consejo Superior De lnvestigaciones Cientificas (CSIC); Martinez Gil, Ana; Gil Ayuso-Gontan, Carmen Belen; Perez Fernandez, Daniel Ignacio; Garcia Fernandez, Ana Maria; (22 pag.)US2016/340320; (2016); A1;,
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Electric Literature of 348-57-2, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 348-57-2, name is 1-Bromo-2,4-difluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 50 To a stirred solution of 2,5-dibromopyridine (30 g, 126.5 mmol) in toluene (1.5 L) was added w-BuLi (1.6 M solution in hexane; 79 mL, 126 mmol) dropwise at -78 °C under an inert atmosphere. After being stirred for 40 min at -78 °C, diethyl oxalate (20.6 mL, 126.5 mmol) was added to the reaction mixture at -78 °C and stirring was continued for another 20 min. After completion of the reaction (by TLC), the reaction mixture was quenched with satd NH4CI solution and extracted with EtOAc (2 x 1.0 L). The combined organic extracts were washed with water and brine, dried over anhydrous Na2S04 and concentrated under reduced pressure to obtain the crude product. The crude material was purified by silica gel column chromatography (eluting with EtOAc/hexane) to afford BK (13 g, 50.37 mmol, 38percent). 1H NMR (200 MHz, CDC13): delta 8.81 (d, J = 1.4 Hz, 1H), 8.17-7.98 (m, 2H), 4.48 (q, J = 7.4 Hz, 2H), 1.41 (t, J = 7.4 Hz, 3H). MS (ESI): m/z 259 [M+l]+.To a stirred solution of BK (13 g, 50.3 mmol) in THF (150 mL) was added methyl magnesium chloride (CH3MgCl, 3 M solution in THF; 15 mL, 50.3 mmol) at -5 °C under an inert atmosphere. Stirring was continued for another 2 h. Progress of the reaction was monitored by TLC. The reaction mixture was then quenched with satd NH4C1 solution and extracted with EtOAc (2 x 200 mL). The combined organic extracts were washed with water and brine, dried over anhydrous Na2S04 and concentrated under reduced pressure to obtain the crude product. The crude material was purified by silica gel column chromatography (eluting with EtOAc/hexane) to afford BL (2.8 g, 10.76 mmol, 21percent). 1H NMR (200 MHz, CDC13): delta 8.61 (d, J = 1.4 Hz, 1H), 7.84 (dd, J = 8.0, 1.4 Hz, 1H), 7.49 (d, J = 8.0 Hz, 1H), 4.92 (br s, 1H), 4.20 (q, J = 1.4 Hz, 2H), 1.80 (s, 3H), 1.22 (t, J = 1.4 Hz, 3H).To a stirred solution of BL (2.8 g, 10.7 mmol) in CH2C12 (50 mL) was added DAST (3.5 mL, 26.5 mmol) at 0 °C under an inert atmosphere, and the reaction mixture was stirred for 16 h at RT. Progress of the reaction was monitored by TLC. The reaction mixture was then quenched with ice-cold water and extracted with CH2C12 (2 x 100 mL). The combined organic extracts were washed with water and brine, dried over anhydrous Na2S04 and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography (eluting with EtOAc/hexane) to afford BM (2.1 g, 7.6 mmol, 75percent). 1H NMR (200 MHz, CDCI3): delta 8.62 (d, J = 1.4 Hz, 1H), 7.85 (dd, J = 8.0, 1.4 Hz, 1H), 7.50 (d, J = 8.0 Hz, 1H), 4.23 (q, J = 1.4 Hz, 2H), 1.95 (d, J F>H = 24.0 Hz, 3H), 1.24 (t, J = 1.4 Hz, 3H). MS (ESI): m/z 276 [M]+.To a stirred solution of l-bromo-2,4-difluorobenzene (0.9 mL, 8.01 mmol) in Et20 (50 mL) was added dropwise w-BuLi (1.6 M solution; 5 mL, 8.01 mmol) at -78 °C under an inert atmosphere. After being stirred for 40 min at -78 °C, a solution of BM (2.1 g, 8.01 mmol) in Et20 (50 mL) was added dropwise to the reaction mixture at -78 °C. Stirring was continued for another 20 min. After completion of the reaction (by TLC), the reaction mixture was quenched with satd NH4C1 solution and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried over anhydrous Na2S04 and concentrated under reduced pressure to obtain the crude product. The crude material was purified by silica gel column chromatography (eluting with EtOAc/hexane) to afford ketone BN (2.15 g, 6.24 mmol, 77.9percent). 1H NMR (200 MHz, CDC13): delta 8.61 (d, J = 1.6 Hz, 1H), 7.96 (dd, J = 8.0, 1.6 Hz, 1H), 7.67-7.62 (m, 1H), 7.48 (d, J = 8.0 Hz, 1H), 6.98-6.67 (m, 2H), 1.98 (d, J F>H = 24.0 Hz, 3H). MS (ESI): m/z 343.9 [M+l]+.To a stirred solution of ketone BN (2.1 g, 6.10 mmol) in CH3CN (30 mL) were added iodotrimethylsilane (TMS-I; 1.47 g, 6.71 mmol) and KOH (683 mg, 12.20 mmol) at RT under an inert atmosphere. The resulting reaction mixture was heated to 70 °C and stirred for 1.5 h; progress of the reaction was monitored by TLC. The reaction mixture was then diluted with EtOAc, stirred for 5 min and filtered; the filtrate was concentrated under reduced pressure to obtain the crude product. The crude material was purified by silica gel column chromatography (eluting with EtOAc/hexane) to afford epoxide BO (1.92 g, 5.36 mmol, 88percent) as a mixture of diastereomers. The product was confirmed by 1H-NMR spectral analysis and was taken forward to the next step without any further purification.To a stirred solution of compound BO (250 mg, 0.7 mmol) in DMF (10 mL) was added 1H- tetrazole (73 mg, 1.05 mmol) followed by K2C03 (96 mg, 0.7 mmol) at RT under inert atmosphere. The resulting reaction mixture was heated to 65 °C and stirred for 48 h. After consumption of the starting material (by TLC), the reaction mixture was cooled to RT, diluted with water (50 mL) and extracted with EtOAc (2 x 50 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL), dried over anhydrous Na2S04 and concent…

The synthetic route of 1-Bromo-2,4-difluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIAMET PHARMACEUTICALS, INC.; HOEKSTRA, William, J.; RAFFERTY, Stephen, W.; YATES, Christopher, M.; SCHOTZINGER, Robert, J.; LOSO, Michael; SULLENBERGER, Michael; WO2012/177603; (2012); A2;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 54879-20-8, name is 2-Bromo-3-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H8BrN

2-Bromo-1 -fluoro-3-methylbenzene; A 200 mL round bottom flask, equipped with a magnetic stirring bar, was charged with 2-bromo-3-methylaniline (12.2 g, 65.58 mmol), 113 mL of water, and 17.5 mL of cone. HCI. The mixture was briefly heated to dissolve the solids, then cooled to -10 0C. To the resulting suspension a solution of NaNO2 (5.06 g, 73.38 mmol) in 13 mL of water was added dropwise at -5 to -10 0C. Then 16.8 mL of 60% HPF6 in water (122.23 mmol) was added, and the resulting suspension was stirred for 30 min. The precipitate was collected by vacuum filtration, washed with ice-cold water (2×30 mL), then with an ice-cold MeOH/ether (16mL/64mL) mixture and dried under vacuum at room temperature for 20 h to give 20.46 g (91%) of diazonium salt. The dry salt was thermally decomposed in 5 g batches in a small (25 mL) vacuum distillation apparatus under vacuum (2 mm Hg), at 165-175 0C, with receiving flask cooled with a dry ice/acetone mixture. The collected fractions were combined to give 7.85 g of 2-bromo-1 -fluoro-3-methylbenzene as a colorless oil. 1H NMR (300 MHz, CDCI3): delta 7.16 (1H), 6.92-7.04 (2H), 2.43 (3H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 54879-20-8.

Reference:
Patent; PFIZER INC.; WO2006/51410; (2006); A1;,
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These common heterocyclic compound, 39478-78-9, name is 5-Bromo-2-methylaniline, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. SDS of cas: 39478-78-9

General procedure: An equimolar mixture of isatin/5-bromoisatin and an aromatic primary amine were introduced into an Erlenmeyer flask. Ethanol (1 mL) and a few drops of acetic acid were added. The Erlenmeyer flask was placed in an ultrasonic bath filled with water (80 Hz,100%), the temperature was adjusted at 40C. At the end of the reaction (monitored by TLC), the product obtained by filtration was recrystallized from ethanol. For the reactions carried out in microwave Biotage, the reagents in 4 mL of ethanol were put in a magnetic stir bar for 2-5 mL vial and the temperature was set at 150C, 160C then 180C.

The synthetic route of 5-Bromo-2-methylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chemchem, Meryem; Menacer, Rafik; Merabet, Naima; Bouridane, Hamida; Yahiaoui, Samir; Moussaoui, Sadjia; Belkhiri, Lotfi; Journal of Molecular Structure; vol. 1208; (2020);,
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Some common heterocyclic compound, 17247-58-4, name is (Bromomethyl)cyclobutane, molecular formula is C5H9Br, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Safety of (Bromomethyl)cyclobutane

A stirred solution of ketimine 10.01 (50 g, 187.1 mmol) under N2 in dry THF (400 mL) was cooled to-78 C and treated with 1 M solution of K-tBuO (220 mL, 1.15 equiv. ) in THF. The reaction mixture was warmed to 0 C and stirred for 1 h and treated with bromomethyl cyclobutane (28 mL, 249 mmol). The reaction mixture was stirred at room temperature for 48 h and concentrated in vacuo. The residue was dissolved in Et20 (300 mL) and treated with aq. HCI (2 M, 300 mL) The resulting solution was stirred at room temperature for 5 h and extracted with Et20 (1 L). The aqueous layer was made basic to pH-12-14 with NaOH (50 % aq. ) and extracted with CH2CI2 (3×300 mL). The combined organic layers were dried (MgS04), filtered, and concentrated to give the pure amine (10.02, 18 g) as a colorless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17247-58-4, its application will become more common.

Reference:
Patent; SCHERING CORPORATION; WO2005/85197; (2005); A1;,
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Application of 586-61-8, A common heterocyclic compound, 586-61-8, name is 1-Bromo-4-isopropylbenzene, molecular formula is C9H11Br, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A suspension of 128.8 g (0.8 mol) of 1H-indole-2-carboxylic acid, of 159.2 g (0.8 mol) of 4-bromocumene, of 111.6 g (0.808 mol) of potassium carbonate and of 8 g (0.1 mol) of copper oxide in 200 ml of dimethylformamide is stirred at reflux for 24 hours. After cooling, 6 l of water are added to the beige suspension obtained. The suspension is filtered and then the insoluble material is taken up in 1 l of a 5N hydrochloric acid solution. This mixture is extracted with 500 ml of dichloromethane. The organic phase is washed with water, dried over sodium sulfate and then concentrated under reduced pressure. After drying under reduced pressure, 204.4 g of a white solid are obtained, which solid is used as is in the following stage. Melting point=203-204 C.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; SANOFI-AVENTIS; US2007/149602; (2007); A1;,
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Application of 2695-48-9, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 2695-48-9, name is 8-Bromo-1-octene, This compound has unique chemical properties. The synthetic route is as follows.

A 250-mL round-bottom flask equipped with a stir bar and a water-jacketed reflux condenser was charged with trimethylsilylacetylene (6.00 mL, 42.0 mmol). THF (50 mL) was added, and the mixture was allowed to cool to 0 C (ice-bath). nButyllithium (29.0 mL, 42.0 mmol, 1.46 M solution in hexanes) was added dropwise by a syringe, and the ice-bath was removed following the addition. The mixture was allowed to warm to 22 C as it stirred for 1 h, at which point 8-bromo- l-octene (3.50 mL, 21.0 mmol) was added, and the mixture was allowed to reflux for 12 h. The mixture was allowed to cool to 0 C, quenched by addition of 50 mL water, washed with CH2CI2 (5 x 50 mL). The combined organic layers were washed in brine ( 1 x 50 mL), dried over MgS0 , filtered, and concentrated in vacuo. The resulting brown oil was filtered through a plug of silica gel (eluted in pentane), the filtrate was concentrated and the resulting brown oil distilled under vacuum ( 1.0 torr). The resulting yellow oil was re-distilled under vacuum ( 1.0 torr) to afford dec-9-en- l -ynyltrimethylsilane (0.700 g, 3.40 mmol, 14.0% yield) as a colorless oil. IR (neat): 3078 (w), 2929 (m), 2857 (w), 2175 (m), 1641 (w), 1461 (w), 1325 (w), 1248 (m), 1032 (w), 994 (w), 910 (m), 837 (s), 758 (s), 725 (w), 697 (w), 638 (m), 575 (w), 450 (w); NMR (400 MHz, CDCb): delta 5.86-5.76 ( 1 H, m), 4.99 ( 1 H, dd, J= 17.2, 2.0 Hz), 4.93 ( 1 H, dd, J= 10.0,0.8 Hz), 2.21 (2H, t, J= 7.2 Hz), 2.05 (2H, app q, J= 7.1 Hz), 1.55- 1.48 (2H, m), 1.40- 1.28 (6H, m), 0. 14 (9H, s); , 3C NMR ( 100 MHz, CDCI 3 ) : delta 1 39.2, 1 14.4, 107.8, 84.4, 33.9, 28.9, 28.8, 28.7, 28.7, 20.0, 0.3 ; HRMS (EST) [M+HJ+ calcd for C^H^Si: 209.1726, found: 209.1719.

The chemical industry reduces the impact on the environment during synthesis 8-Bromo-1-octene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; TRUSTEES OF BOSTON COLLEGE; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; HOVEYDA, Amir, H.; MEEK, Simon, J.; O’ BRIEN, Robert, V.; CROS, Josep, Llaveria; SCHROCK, Richard, R.; WO2011/97642; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 766-81-4, name is 3-Bromophenylacetylene, belongs to bromides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 766-81-4, category: bromides-buliding-blocks

The 3′-bromophenylacetylene (181 mg, 1.0 mmol), cat. [Au] (6 mg, 1 muM %), AgOTf (2.6 mg, 1 muM %), water (36 mg, 2 mmol) and methanol (1 ml) are added to the 25 mL of Claisen tube or. After closing the reaction at 120 C for 6 hours, cooling to room temperature. Then adding formic acid amine (315 mg, 5 mmol) and cat. [Rh] (6.2 mg, 1 mmol %), the reaction mixture in oil bath heated to 80 C, reaction 12 hours, cooling to room temperature. Rotary evaporation of the solvent and add a certain amount of ethyl acetate and water extraction, the organic phase of the resulting product after concentrated hydrochloric acid the reflux process, rotary evaporation to remove the solvent, the final petroleum ether washing and filtering to obtain the pure target compound, yield: 83%

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Nanjing University of Science and Technology; Li Shun; Xu Meng; Li Feng; (12 pag.)CN109384677; (2019); A;,
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These common heterocyclic compound, 1073-06-9, name is 1-Bromo-3-fluorobenzene, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Recommanded Product: 1-Bromo-3-fluorobenzene

Charge an oven-dried 250 mL round-bottom flask with 6-methoxy-1-tetralone (3. 0g, 17.0 mmol. ) and place under nitrogen. Dissolve the solid in toluene (30mL) and add 1-bromo-3-fluorobenzene (4. 7 mL, 42.6 mmol), sodium t-butoxide (6.5g, 68.1 mmol), palladium acetate (76mg, 0.34 mmol), and racemic BINAP (212mg, 0.34 mmol). Heat the solution to 115C and stir for 18 hours. Dilute the solution with cold 5N HC1 (50mL) and ethyl acetate (200mL). Separate the organic layer and dry over sodium sulfate, filter over a pad of celite and concentrate in vacuo. Purify the crude product using radial chromatography to give 3.4 g (74%) of the title compound. This material is used without further purification: mass spectrum (ion spray) m/z =267 (M-H). Dissolve 2- (3-fluoro-phenyl)-6-methoxy-naphthalen-l-ol (3.36g, 12.5 mmol) in N-methyl-2-pyrrolidinone (NMP) (lOmL) and add sodium hydride (500mg, 60% oil dispersion, 12.5 mmol) at room temperature. After stirring for 1 hour this solution is added to a solution of 4-fluorobenzaldehyde (2.4mL, 22.5 mmol) in NMP (lOmL) that has been heated to 185C. Continue stirring for 2.5 hours. Cool the reaction to room temperature and add pH 7 buffer (50mL) and extract with ethyl acetate (2 X 100mL). Wash the organic extracts with water and filter through a plug of silica gel. Purify the crude product using radial chromatography giving 2. 50g (54%) of the title compound and use without further purification: mass spectrum (ion spray) m/z = 371 (M-H). Charge a 100 mL round-bottom flask with 4- [2- (3-fluoro-phenyl)-6-methoxy- naphthalen-l-yloxy]-benzaldehyde (2. 5g, 6.71 mmol) and ethyl acetate (5 mL). At room temperature add 2 mL of 35% hydrogen peroxide. To this solution slowly add 2 mL of concentrated sulfuric acid. The mixture warms to approximately 40 C and returns to room temperature where it is stirred for 2 hours. Dilute the reaction with water and ethyl acetate (100 mL) and dry the organic layer over sodium sulfate, filter and concentrate in vacuo. Purify the crude product using radial chromatography eluting with CH2C12 to yield 540 mg (22%) of the title compound: mass spectrum (ion spray) m/z = 359 (M-H).

The synthetic route of 1-Bromo-3-fluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/73204; (2005); A1;,
Bromide – Wikipedia,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 556-96-7, name is 1-Bromo-3,5-dimethylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 556-96-7

General procedure: In an oven dried round bottomed flask a mixture containing styrene (2.5mmol), aryl halide (2.5mmol), the palladium complex [Pd(OL1)]4 (0.005mmol) and potassium carbonate (10.0mmol) in methanol (10cm3) was heated to reflux for 4h, as mentioned in Table 3. After the reaction was completed, the solvent was evaporated and the reaction mixture was extracted with diethyl ether. The ether solution was dried over Na2SO4 and filtered. The ether solution, containing the reaction mixture, was passed through a 12.48cm silica column (60-120 mesh), the complex was not separated out and it remained trapped in the column. After he desired compound was extracted from the column, the complex was eluted using dichloromethane. Upon evaporation of the ether, solids of the pure products were obtained. The yields of the products obtained from all the reactions were determined after isolation, and the products were characterized by 1H NMR spectra.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 556-96-7.

Reference:
Article; Pattanayak, Poulami; Pratihar, Jahar Lal; Patra, Debprasad; Lin, Chia-Her; Chattopadhyay, Surajit; Polyhedron; vol. 63; (2013); p. 133 – 138;,
Bromide – Wikipedia,
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