Tag: M.W=200-300

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. 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1,3-Dibromo-5-fluorobenzene

EXAMPLE 5 (3-Bromo-5-fluorophenyl)-4,4-dimethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one Procedure B A mixture of (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid (2.22 g, 10 mmol), 1,3-dibromo-5-fluorobenzene (3.05 g, 12 mmol), tetrakis(triphenylphosphine)palladium (0) (0.6 g, 0.52 mmol), and sodium carbonate (2.2 g, 21 mmol) in a mixture of DME and water (70 mL/15 mL) was degassed to remove the oxygen and then heated at 85 C. under a blanket of nitrogen for 3 hours. The reaction mixture was cooled to ambient temperature and quenched with a saturated aqueous ammonium chloride solution (20 mL). Ethyl acetate (100 mL) was added and organic layer was separated. The aqueous layer was extracted with ethyl acetate (3*30 mL). The combined organic layers were washed with brine and dried with MgSO4. The solvent was removed in vacuo and the residue was purified by a silica gel flash chromatography (hexane:ethyl acetate/1:1) to give 6-(3-bromo-5-fluorophenyl)-4,4-dimethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one as a white solid (1.4 g, 40%): mp 182-183 C.; 1H-NMR (DMSO-d6) delta10.36 (s, 1H, D2O exchangeable), 7.78 (s, 1H), 7.58-7.65 (m, 3H), 7.49 (dd, 1H, J=8.3, 1.8 Hz), 6.96 (d, 1H, J=8.5 Hz), 1.69 (s, 6H); 19F-NMR (DMSO-d6) delta-112.46 (m, 1F); MS (CI) m/z 352([M+H]+, 78%), 350([M+H]+, 75%). Anal. Calc. For C16H13BrFNO2: C, 54.88; H, 3.74; N, 4.00. Found: C, 54.83; H, 3.82; N, 3.95.

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; Wyeth; Ligand Pharmaceuticals, Inc.; US6436929; (2002); B1;,
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Synthetic Route of 129316-09-2, These common heterocyclic compound, 129316-09-2, name is 1,3-Dibromo-5-(tert-butyl)benzene, 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.

Step 1 : 1-Bromo-3-(tert-butyl)-5-(prop-1-en-2-vnbenzene (P24a)To a solution of 1 ,3-dibromo-5-(terf-butyl)benzene (2.92 g, 10 mmol) in dioxane (20 mL) was added Pd(PPh3)4 (3.0 g, 2.6 mmol), prop-1-en-2-ylboronic acid (1.0 g, 12 mmol), K2C03 (2.8 g, 20 mmol) and H20 (1 mL) under N2. The resulting mixture was stirred at 90C overnight, concentrated and purified by CC (hexane) to give compound P24a (2.5 g, 100%; 80% by GC/MS) as a liquid.

Statistics shows that 1,3-Dibromo-5-(tert-butyl)benzene is playing an increasingly important role. we look forward to future research findings about 129316-09-2.

Reference:
Patent; PHENEX PHARMACEUTICALS AG; STEENECK, Christoph; KINZEL, Olaf; GEGE, Christian; KLEYMANN, Gerald; HOFFMANN, Thomas; WO2012/139775; (2012); A1;,
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Reference of 1435-53-6, 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. 1435-53-6, name is 2,4-Dibromo-1-fluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Dibromofluorobenzene (1.0 g, 4.0 mmol), sodium methanethiolate (0.33 g, 4.8 mmol) and triethylamine (0.52 mL, 4.0 mmol) were dissolved in a flask charged with 3 mL of N,N-dimethylacetamide in a sealed tube and heated to 100 C for 12 hours. After the reaction was completed, the reaction solution was cooled to room temperature, extracted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and passed through a silica gel column (ethyl acetate / n-hexane) to give an oily liquid (0.65 g, 58%).

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

Reference:
Patent; South China University of Technology; Yang Wei; Yang Yong; Zhang Bin; Wu Hongbin; Cao Yong; (32 pag.)CN105001233; (2017); B;,
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Synthetic Route of 58971-11-2,Some common heterocyclic compound, 58971-11-2, name is 3-Bromophenethylamine, molecular formula is C8H10BrN, 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.

N-3-brornophenethyB-2,2,2-trifhioroacetamk1e. A vial was charged with 2(3bromophenyflethanamine (600 nig, 3 mnrol). methylene chloride (2.0 mL), and tri.tluoroacetie anhydride:0 4 niL 3 mmd) lrwthvlamine (0 X4 mL 6 mmd) xas carttull iddtd dtopxs ist I Ia rcxtmn n?is stirred for 1 h then concentrated. The residue was purified on silica gel (20% EtOAc/hexanes) to provide the hUe compound (773 mg, 87% yield). LCMS: Ri? 1.007 miii; M+H 296.2..

The synthetic route of 58971-11-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VANDERBILT UNIVERSITY; CONN, Jeffrey, P.; HOPKINS, Corey, R.; LINDSLEY, Craig, W.; NISWENDER, Colleen, M.; EMMITTE, Kyle; BRONSON, Joanne; WU, Yong-Jin; PANARESE, Joe; ENGERS, Darren, W.; ENGERS, Julie; (136 pag.)WO2016/123627; (2016); 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. 30273-40-6, name is 4-Bromo-2,5-dimethylaniline, A new synthetic method of this compound is introduced below., Product Details of 30273-40-6

Example 65-Chloro-N2-(2,5-dimethyl-4-(morpholinomethyl)phenyl)-A/4-(5-methyl-lH- pyrazol-3-yl)pyrimidine-2,4-diamine (39) [0113] Step 1: A mixture of 2,5-dichloro-N-(5-methyl-lH-pyrazol-3-yl)pyrimidin- 4-amine (732 mg, 3 mmol), 4-bromo-2,5-dimethylaniline (554 mg, 2 mmol) and cone, aqueous HCl (1.5 mL) in isopropanol (15 mL) was heated in a microwave for 40 min at 130 C. LCMS showed that the reaction was not complete, and additional 2,5- dichloro-N-(5-methyl-lH-pyrazol-3-yl)pyrimidin-4-amine (732 mg, 3 mmol) was added to the reaction. The reaction was again heated in a microwave for an additional 60 min at 130 C. The crude reaction mixture was then diluted with EtOAc (100 mL), sequentially washed with saturated aqueous NaHCO3 (2×20 mL) and brine (10 mL), dried over Na2CO3 and concentrated in vacuo. The crude product was purified by silica chromatography (0-10% MeOH in EtOAc gradient with 1% NH3 additive) to give Lambdaf2-(4-bromo-2,5-dimethylphenyl)-5-chloro-Lambda^-(5-methyl-lH-pyrazol-3- yl)pyrimidine-2,4-diamine as an off-white solid; ESMS m/z 407.2 (M+H+).

The synthetic route of 30273-40-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; WO2009/158431; (2009); A2;,
Bromide – Wikipedia,
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Electric Literature of 626-40-4, These common heterocyclic compound, 626-40-4, name is 3,5-Dibromoaniline, 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.

Compound 2i was synthesized following a procedure published for the preparation of similar compounds.1 To a mixture of 3,5-dibromoaniline (0.22 g, 0.87 mmol) and Et3N (0.12 mL, 0.87 mmol) in anhydrous CH2Cl2 (10 mL), 2,2′-dithiobenzoyl chloride (1, 0.30 g, 0.87 mmol) in anhydrous CH2Cl2 (20 mL) was added dropwise over 15 min. The reaction mixture was stirred for 3 h at rt, and washed with 1 M HCl (50 mL), H2O (50 mL), and brine (50 mL). The organic layer was dried over anhydrous MgSO4, concentrated in vacuo, and the residue was purified by flash column chromatography (SiO2, 1:4/EtOAc:hexanes) and recrystallized in EtOH to afford compound 2i (135 mg, 33%, Rf 0.31 in 1:4/EtOAc:hexanes) as a white solid: 1H NMR (400MHz, CDCl3, Fig. S13) delta 8.08 (d, J = 8.0 Hz, 1H), 7.89 (s, 2H), 7.68 (t, J = 6.8 Hz, 1H), 7.58 (s,1H), 7.57 (d, J = 8.0 Hz, 1H), 7.45 (t, J = 8.0 Hz, 1H); 13C NMR (100 MHz, CDCl3, Fig. S14) delta164.3, 139.7, 139.6, 133.2, 132.5, 127.6, 126.4, 125.8, 124.5, 123.5, 120.4; LRMS m/z calcd forC13H7Br2NOS: 385.1; found 386.1 [M+H]+.

The synthetic route of 626-40-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ngo, Huy X.; Shrestha, Sanjib K.; Green, Keith D.; Garneau-Tsodikova, Sylvie; Bioorganic and Medicinal Chemistry; vol. 24; 24; (2016); p. S1 – S53;,
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Some common heterocyclic compound, 141474-37-5, name is 2,4-Dibromo-6-fluoroaniline, molecular formula is C6H4Br2FN, 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. Product Details of 141474-37-5

5.38g (20.0 mmol) of 2,4-dibromo-6-fluoro-phenylamine, 5.36 g (44.0 mmol) of phenylboronic acid, 1.15 g (1.0 mmol) of Pd(PPh3)4, and 8.29 g (60.0 mmol) of K2CO3 were dissolved in 80 mL of a mixed solution THF/H2O (2:1) to obtain a solution, which was then stirred at about 70C for about 5 hours. The reaction solution was cooled to room temperature, followed by three times of extraction with 60 mL of water and 60 mL of diethylether. The organic phase was collected, and was dried using magnesium sulfate to evaporate the solvent. The residue was separated and purified using silica gel column chromatography to obtain 4.11 g of Intermediate I-29 (Yield: 78 %) This compound was identified using LC-MS and NMR. C18H14FN : M+ 263.1 1H NMR (CD2Cl2, 400MHz) delta (ppm) 7.62-7.57 (t, 1H), 7.56-7.54 (m, 1H), 7.51-7.47 (m, 4H), 7.44-7.37 (m, 3H), 7.31-7.30 (m, 1H), 7.29-7.26 (m, 1H), 7.23-7.22 (m, 1H), 3.94 (s, 2H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 141474-37-5, its application will become more common.

Reference:
Patent; Samsung Mobile Display Co., Ltd.; EP2447250; (2012); 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. 627871-16-3, name is 5-Bromo-4-fluoro-2-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 627871-16-3

WXBB-1-4a (20.00 g, 98.02 mmol, 1.00 eq) was dissolved in N-methylpyrrolidone (100.00 mL), followed by addition of cuprous cyanide (17.56 g, 196.04 mmol, 42.83 mL, 2.00 eq). The reaction was carried out at 180C for 3 hours. The reaction solution was cooled to room temperature, followed by addition of water (300 mL) and ammonia (300 mL), stirred at room temperature for 30 minutes, and extracted with ethyl acetate (200 mL 3). The organic phase was washed with saturated brine (200 mL) and water (200 mL), dried over anhydrous sodium sulfate, suction-filtered and rotary evaporated to dry under reduced pressure to give a crude product as a brown-black solid. The crude product was isolated by silica gel column chromatography (PE: EA=20:1-3:1) to give WXBB-1-4 (12.00 g, 79.92 mmol, 81.53% yield) as a yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 2.21 (s, 3 H) 3.68 (br s, 2 H) 6.80 (d, J=5.40 Hz, 1 H) 6.91 (d, J=9.29 Hz, 1 H).

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 627871-16-3.

Reference:
Patent; Fujian Cosunter Pharmaceutical Co., Ltd.; WU, Chengde; YU, Tao; LI, Ning; CHEN, Shuhui; (58 pag.)EP3572412; (2019); 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. 59734-92-8, name is 1-Bromo-2-cyclohexylbenzene, This compound has unique chemical properties. The synthetic route is as follows., category: bromides-buliding-blocks

A Schlenk tube was charged with Cul (9.6 mg, 0.050 mmol, 5.0 mol%), NaI (300 mg, 2.00 mmol), evacuated and backfilled with argon. Racemic [TRANS-N, N’-DIMETHYL-1,] 2- cyclohexanediamine (16 RL, 0.10 mmol, 10 mol%), 1-bromo-2-cyclohexylbenzene (97% pure; Lancaster; 186 [(IL,] 1.00 mmol), n-pentanol (1 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at [130 C] for 40 h. The resulting suspension was allowed to reach room temperature and filtered through silica gel (1 x0. 5 cm) eluting with hexane (50 mL). The filtrate was concentrated, and the residue was purified by flash chromatography on silica gel (hexane) to provide the known [1-IODO-2-CYCLOHEXYLBENZENE] (283 mg, 99% yield; ca. 97% pure) as a colorless liquid. [SEE MCGUINE,] T. H.; Dull, M. F. J. Am. [CHEM. SOC.] 1947, 69, [1469.’H NMR] (400 MHz, [CDC13)] : 8 7. 85 (dd, [J= 7.] 5,1. [2 HZ,] 1H), 7.32 (td, J= 7.5, 1. [2 HZ,] 1H), 7.23 (dd, [J= 7.] 5,1. [7 HZ,] 1H), 6.90 [(TD,] [J= 7.] 5,1. [7 HZ,] 1H), 2.81 (tt, J= 11.7, 3. [0 HZ, 1H),] 1.97-1. 74 (m, [5H),] 1.55-1. 23 (m, [5H).] [13CNMR] (100 MHz, [CDC13)] : 8 149.3, 139.5, 128.4, 127.6, 126.6, 101.5, 48. 5,33. 4,26. 8,26. 1.

According to the analysis of related databases, 59734-92-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; WO2004/13094; (2004); A2;,
Bromide – Wikipedia,
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These common heterocyclic compound, 28342-75-8, name is 1,5-Dibromo-2,4-difluorobenzene, 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. Product Details of 28342-75-8

38. Preparation of 1-bromo-2,4-difluoro-5-methoxybenzene; To a solution of 1,3 dibromo-4,6-difluorobenzene (10.0 g, 37 mmol) in THF (50 mL) at -20° C. was added isopropyl magnesium chloride (2.0M in THF, 42 mmol) and the resulting solution warm to 0° C. and stirred for 30 minutes. Trimethylborate (4.7 g, 45 mmol) was added and the mixture stirred at ambient temperature for 1 hour. The solution was recooled to -20° C. and peracetic acid (32percent, 50 mmol) was added and the solution was stirred for 30 minutes at ambient temperature. The solution was then quenched with sodium bisulfite (5percent solution, 75 mL) and then acidified with 6 N hydrochloric acid and extracted with ethyl ether (2.x.75 mL). Combined extracts were dried (sodium sulfate) and concentrated. The crude phenol was dissolved in acetonitrile (40 mL) and potassium carbonate (10 g, 74 mmol) and iodomethane (5.7 g, 40 mmol) were added and stirred at ambient temperature for 20 hours. The solution was concentrated and the residue taken into water (50 mL) and extracted with ethyl ether (2.x.75 mL) and the combined extracts were washed with brine, dried (sodium sulfate), and concentrated. The residue was purified by chromatography (hexanes) to give 1-bromo-2,4-difluoro-5-methoxybenzene (2.0 g, 8.6 mmol): LC/MS (m/z=223).

The synthetic route of 1,5-Dibromo-2,4-difluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Balko, Terry W.; Schmitzer, Paul R.; Daeuble, John F.; Yerkes, Carla N.; Siddall, Thomas L.; US2007/179060; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary