Category: bromides-buliding-blocks

Electric Literature of 1435-51-4,Some common heterocyclic compound, 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, molecular formula is C6H3Br2F, 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.

Sodium methoxide (4.5M solution in methanol, 8.80 [ML,] 41.0 [MMOL)] was added dropwise to a stirred solution of 3, 5-dibromofluorobenzene (5.00 g, 19.0 [MMOL)] in [N, N-DIMETHYLFORMAMIDE] (95 ml) at [0C] under a nitrogen atmosphere. The reaction was warmed to room temperature, stirred for 1 hour and then evaporated under reduced pressure. The residue was dissolved in diethyl ether and was washed with water [(3X300] [ML)] and brine (300 [ML),] dried over magnesium sulphate, filtered and concentrated under reduced pressure to give the title compound as a white solid (5.13 g). ‘H-NMR [(300MHZ,] CDC13) : [8] 3.79 (s, 3H), 7.00 (s, 2H), 7.26 (s, [1 H).] LRMS: m/z TS+ 266 [[M+H] +.]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,3-Dibromo-5-fluorobenzene, its application will become more common.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/29051; (2004); A1;,
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Electric Literature of 76153-06-5, These common heterocyclic compound, 76153-06-5, name is 5-Bromo-3-methylbenzene-1,2-diamine, 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.

EXAMPLE 375-Methyl-7-r3-(piperidin-l-ylmethyl)phenyl]quinoxalineGlyoxal (10 drops of a 40% solution in water) was added to a solution of 5- bromo-2,3-diaminomethylbenzene (80 mg, 0.4 mmol) in ethanol (3 mL). The mixture was stirred and left to stand at r.t. for 1 h. The mixture was partitioned between water and EtOAc (20 mL each), and the organic phase was dried (MgSO4) and concentrated in vacuo. The residue was dissolved in DME (1.2 mL), and 3-(piperidin-l-ylmethyl)phenyl- boronic acid pinacol ester hydrochloride (135 mg, 0.4 mmol), 2M aqueous sodium carbonate solution (0.6 mL, 0.9 mmol) and Pd(PPh3)4 (14 mg, 0.012 mmol) were added. The mixture was heated to 1200C in a sealed tube, under microwave irradiation, for 20 minutes. The mixture was partitioned between water and EtOAc (2 mL each), and the organic phase was concentrated in vacuo. The residue was purified by preparative HPLC to give the title compound (5 mg, 4% over the two steps) as a pale yellow-brown gum. delta? (CDCl3) 8.87 (d, IH), 8.85 (d, IH), 8.17 (s, IH), 7.93 (s, IH), 7.72 (s, IH), 7.65 (d, IH), 7.46 (t, IH), 7.39 (d, IH), 3.58 (s, 2H), 2.88 (s, 3H), 2.34-2.52 (m, 4H), 1.51-1.68 (m, 4H), 1.39-1.51 (m, 2H). LCMS (ES+) 318 (M+H)+, RT 2.43 minutes.

Statistics shows that 5-Bromo-3-methylbenzene-1,2-diamine is playing an increasingly important role. we look forward to future research findings about 76153-06-5.

Reference:
Patent; UCB PHARMA S.A.; BUeRLI, Roland; HAUGHAN, Alan, Findlay; MACK, Stephen, Robert; PERRY, Benjamin, Garfield; RAPHY, Gilles; SAVILLE-STONES, Elizabeth, Anne; WO2010/52448; (2010); A2;,
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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 7617-93-8 as follows. HPLC of Formula: C8H3BrF6

2,5-BIS (TRIFLUOROMETHYL) BROMOBENZENE (0.59 G, 2.00 MMOL, 1.00 EQUIV. ), 4- nitrophenylbronic acid (0.334 g, 2. 00 mmol, 1.00 equiv. ), trans- benzyl (chloro) bis (TRIPHENYLPHOSPHINE) PALLADIUM (LL) (0.076 g, 0.10 mmol, 0.05 EQUIV.), K2CO3 1.38 g, 10.00 MMOL, 5.00 equiv. ) and 10 mL dry NMP were charged to a 25 mL round bottom flask. The mixture was thoroughly de- oxygenated by subjecting to vacuum/nitrogen cycle three times, and heated at 110 C for 2 days under nitrogen protection. Usual workup yielded crude product 4′-nitro-2, 5-bis-trifluoromethyl-biphenyl as brown viscous oil (0. 66 g, 1.97 mmol, 99%). H NMR (300 MHz, CDCl3), 6 (ppm): 8.32 (d, J = 8.7 Hz, 2H); 7. 82-8. 00 (m, 2H); 7.52-7. 61 (m, 3H).The crude product made in the last step was dissolved in 10 mL methylene chloride and 10 mL ethanol. Tin (II) CHLORIDE (2.28 g, 12.00 mmol, 6.00 equiv) was added, followed by addition of 1 mL water. After stirring at room temperature for 2 days, the mixture was neutralized with 2 N NAOH solution, and subjected to usual workup to yield crude product 4′-amino-2, 5-bis-trifluoromethyl- biphenyl (0.52 g, 1.70 mmol, 85% crude yield) as brown viscous oil.4′-Amino-2, 5-bis-trifluoromethyl-biphenyl (0.16 g, 0.50 mmol, 1.00 equiv) was dissolved in 10 mL methylene chloride. To the solution was added 2,3- DIFLUOROBENZOYL chloride (0. 088 g, 0.50 mmol, 1.00 equiv), and triethylamine (0.061 g, 0.60 mmol, 1.20 equiv). The mixture was stirred at room temperature for one hour, and loaded to column for flash chromatography. The title compound was isolated as light yellow solid (0.12 g, 0.27 mmol, 54%). 1H NMR (300 MHz, CDCI3), 6 (PPM) : 8. 39 (D, J= 10.5 Hz, 1H) ; 7.75-7. 95 (m, 6H); 7.63 (s, 1H); 7.26-7. 443 (m, 3H); ESMS CALCD. FOR C21H12F8NO (M + H) + : 446.0 ; Found: 446.0

According to the analysis of related databases, 7617-93-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNTA PHARMACEUTICALS, CORP.; WO2005/9954; (2005); A2;,
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Adding a certain compound to certain chemical reactions, such as: 54962-75-3, name is 3-Bromo-5-(trifluoromethyl)aniline, 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 54962-75-3, Product Details of 54962-75-3

Step A: Preparation of {3-[3-amino-5(trifluoromethyl)phenyl]propynyl}dimethylamine A mixture of 3-bromo-5-trifluoromethylaniline (1.4 g, 5.9 mmol), 1-dimethylamino-2-propyne (1.3 mL, 0.76 mmol), PdCl2(PPh3)2 (0.26 g, 0.29 mmol) and CuI (114 mg, 0.60 mmol) in 10 mL of TEA was heated at 100 C. in a sealed tube for 3 h. The resulting mixture was filtered over Celite. The filtrate was concentrated, and the residue was purified by prep-HPLC (reverse phase) to give the aniline. MS (ES+): 243 (M+H)+; (ES-): 241 (M-H)-. Calc’d C12H13F3N2-242.24.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3-Bromo-5-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chen, Guoqing; Adams, Jeffrey; Bemis, Jean; Pietro, Lucian Di; Dominguez, Celia; Elbaum, Daniel; Germain, Julie; Huang, Qi; Kim, Joseph L.; Ouyang, Xiaohu; Patel, Vinod F.; Smith, Leon M.; Tasker, Andrew; Xi, Ning; Xu, Shimin; Yuan, Chester Chenguang; Croghan, Michael; Kim, Tae-Seong; US2003/195230; (2003); A1;,
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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. 16518-62-0, name is 3-Bromo-N,N-dimethylaniline, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 16518-62-0

3-Bromo-/V,/V-dimethylaniline (13) (3.20 g, 16.00 mmol, 2.0 eq.) was dissolved in dry Et20 (45 mL) and cooled down to -78 C. sec-BuLi (14.0 mL, 18.40 mmol, 2.3 eq., 1.3 M in cyclohexane) was added dropwise over 15 min and the mixture was stirred for 30 min at – 78 C. Dichlorodimethylsilane (14) (1.0 mL, 8.00 mmol, 1.0 eq.) was added dropwise over 10 min at -78 C. The mixture was stirred for 10 min at -78 C and then warmed up to room temperature and stirred for 1 h. The mixture was quenched with aqueous saturated NaHCC>3 solution. The aqueous layer was extracted with Et20 (3 x 150 mL) and the combined organic layers were dried over MgS04, filtered and evaporated to afford the crude product.

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 16518-62-0.

Reference:
Patent; SPIROCHROME AG; JOHNSSON, Kai; REYMOND, Luc; FREI, Michelle; PITSCH, Stefan; (71 pag.)WO2019/122269; (2019); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 53078-85-6, name is 2-Bromo-5-methylaniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Bromo-5-methylaniline

A mixture of compound 36b (3 3 g, 17 7 mmol), glycerin (3 3 g, 35 5 mmol), nitrobenzene (2 2 g, 17 7 mmol) and 75% aqueous sulfuric acid (10 mL, 138 mmol) is stirred at 15O0C for 3 h (mixture turns black and viscous) The reaction mixture is cooled down, poured into ice-water (200 mL) and 10 N aqueous NaOH is added (30 mL, 300 mmol) The black mixture is then shaken with EtOAc (100 mL) and is centrifuged in 50 mL portions The upper EtOAc layers are combined and the bottom aqueous layers containing the black tar are shaken with EtOAc and re-cent?fuged All EtOAc extracts are combined, washed with brine, dried over Na2SO4, filtered and concentrated under vacuum to give 4.8 g of a brown-red oil. This material is chromatographed on 80 g silica gel column (CombiFlash Companion apparatus, hexanes/EtOAc gradient). The fractions containing the compound are concentrated under vacuum to afford compound 36c as a white solid (3.26 g, 83% yield).

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; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; CARSON, Rebekah J.; FADER, Lee; KAWAI, Stephen; LANDRY, Serge; WO2009/62288; (2009); A1;,
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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. 2862-39-7, name is 2-Bromo-N,N-dimethylethanamine hydrobromide, This compound has unique chemical properties. The synthetic route is as follows., Safety of 2-Bromo-N,N-dimethylethanamine hydrobromide

A-1 a (500 mg; 2.60 mmol) is dissolved in DMF (5.00 mL) and potassium carbonate (1.26 g; 9.1 1 mmol) is added in one portion. The reaction mixture is stirred at rt for 30 min. (2-bromoethyl)dimethylamine hydrobromide (SM-5d) (788 mg; 3.38 mmol) is added and stirring is continued for 4 h. Water is added and stirring is continued for 18 h. The volatiles are evaporated and the residue is dried in vacuo. The crude mass is triturated with a mixture of EtOH and MeOH (1 :1 ), filtered and washed with EtOH. The filtrate is evaporated and purified by preparative HPLC under basic conditions to give 1 -[2- (dimethylamino)ethyl]-5-nitro-2,3-dihydro-1 H-indole-2,3-dione (A-3e).

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 2862-39-7.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; STEURER, Steffen; DAHMANN, Georg; KERRES, Nina; KOEGL, Manfred; (210 pag.)WO2018/108704; (2018); A1;,
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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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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. 129316-09-2, name is 1,3-Dibromo-5-(tert-butyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1,3-Dibromo-5-(tert-butyl)benzene

Synthesis of 1-(3-bromo-5-tert-butylphenyl)-1H-imidazole 7 A mixture of 1,3-dibromo-5-tert-butylbenzene (2.92 g, 10.0 mmol, 1.0 eq), 1H-imidazole (0.69 g, 10.0 mmol, 1.0 eq), CuI (0.19 g, 1.0 mmol, 0.10 eq), K2CO3 (2.76 g, 20.0 mmol, 2.0 eq) and 2-(dimethylamino)acetic acid (0.21 g, 2.0 mmol, 0.20 eq) in DMSO (10 mL) was stirred at a temperature of 110 C. for four days under a nitrogen atmosphere, then cooled down to ambient temperature. The mixture was diluted with plenty of ethyl acetate and filtered. The filtrate was washed with water three times, dried over sodium sulfate, then filtered, and the filtrate was concentrated under reduced pressure. The residue was purified through column chromatography on silica gel using hexane and ethyl acetate as an eluent to obtain the desired product, 1-(3-bromo-5-tert-butylphenyl)-1H-imidazole 7, as a brown sticky liquid (1.56 g in 56% yield).

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 129316-09-2.

Reference:
Patent; Arizona Board of Regents on behalf of Arizona State University; Li, Jian; Li, Guijie; (116 pag.)US9224963; (2015); B2;,
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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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