Bromides-buliding-blocks

3814-30-0, name is (Bromomethyl)cyclopentane, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 3814-30-0

EXAMPLE 2 Preparation of 1-(cyclopentylmethyl)imidazole A solution of sodium ethoxide was made by dissolving sodium (2.3 g, 0.1 mole) in absolute ethanol (100 ml). Imidazole (6.8 g, 0.1 mole) was then added. The mixture was heated under reflux and cyclopentylmethylbromide (16.3 g, 0.1 mole) was added dropwise. The reaction mixture was allowed to reflux for a further 16 hours after addition. The mixture was then left to cool. The solid material was then filtered off and the filtrate evaporated down under vacuum. The residue was taken up in 2 N HCl (150 ml) and washed with ether (50 ml). The solution was basified with excess 10 N NaOH and the product extracted with chloroform (3*50 ml). Combined extracts were dried over anhydrous MgSO4 and chloroform removed under vacuum to give yellowish oil. The crude product was purified on a silica gel column eluted with EtOAc/MeOH (9:1). The product fractions were combined and evaporated down under vacuum to leave 1.9 g of slightly yellowish oil. This was distilled under vacuum. B.pt. 68-69 C./0.125 mmHg. Yield 0.95 g.

Statistics shows that 3814-30-0 is playing an increasingly important role. we look forward to future research findings about (Bromomethyl)cyclopentane.

Reference:
Patent; Burroughs Wellcome Co.; US4284641; (1981); A;,
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Some common heterocyclic compound, 40161-54-4, name is 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene, molecular formula is C7H3BrF4, 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. 40161-54-4

A mixture of 5 g (20 mmol) 1-BROMO-2-FLUORO-4-TRIFLUOROMETHYL-BENZENE, 4.6 g (24.7 mmol) n-Boc-piperazine, 106 mg (0.1 mmol) Tris (dibenzylideneacetone) DIPALLADIUM chloroform complex 2.77 g (28.8 mmol) sodium-t-butoxide and 144 mg (0.4 mmol) 2- (DICYCLOHEXYLPHOSPHINO) biphenyl in 50 ml toluene was heated for 16 h at 80 C. After cooling to room temperature the mixture was treated with 15 g Isolute HM-N and all volatiles were removed under vacuum. The residue was purified on silica eluting with a gradient of heptane/EtOAc to yield after evaporation 4.54 g (63%) of the title compound as white amorphous solid. 1-H-NMR (300 MHz, CDC13) 8= 7.50 (D, J = 12 Hz, 1H, H-3), 7.48 (d, J = 8 Hz, 1H, H- 5), 7.2 (dd, JI = 8 Hz, J2 = 8 Hz, 1H, H-6), 3.49 (m, 4H, piperazine), 3. 08 (m, 4H, piperazine). MS (m/e): 349.2 (MH+, 100%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 40161-54-4, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2005/23260; (2005); A1;,
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327-52-6, A common heterocyclic compound, 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, molecular formula is C6H2BrF3, 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 22 Dineophyl-2,4,5-trifluorophenyltin chloride (compound 92) Dineophyl-di(2,4,5-trifluorophenyl)tin (113.1 g), a pale-yellow viscous liquid, was prepared in substantial accordance with the procedure described in Example 1 (1) except that 2,4,5-trifluorophenyl bromide (105.9 g, 0.502 mol), rather than metatrifluoromethylphenyl bromide, was employed. Gas chromatography analysis of this liquid showed 96.0% purity. Tin content was 17.8% (theoretical: 18.3%). The above product (76.4 g, 0.118 mol) was then reacted with chlorine and the reaction mixture was worked up in substantial accordance with the procedure described in Example 5. Recrystallization of the product from n-hexane gave 39.3 g of dineophyl-2,4,5-trifluorophenyltin chloride as a white solid.

The synthetic route of 327-52-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi & Co., Ltd.; Nitto Kasei Co., Ltd.; US4774235; (1988); A;,
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327-51-5, These common heterocyclic compound, 327-51-5, name is 1,4-Dibromo-2,5-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.

Under an argon atmosphere, to a solution of 1,4-dibromo-2,5-difluorobenzene (10, 70.00 g) in diethyl ether (500 mL) was added dropwise 1.58 M n-butyl lithium solution in hexane (171 mL) at -78 C, and the mixture was stirred at same temperature for 2 min. The mixture was added quickly to the mixture of dry ice (about 300 g) and diethyl ether (600 mL), and the mixture was warmed up to room temperature. The precipitate was collected by filtration, and washed with diethyl ether. The obtained solid was treated with water (100 mL) and 1 M hydrochloric acid (500 mL), and extracted with diethyl ether. The organic layer was washed with brine and dried. The desiccant was removed by filtration and the filtrate was evaporated in vacuo. The resulting residue was washed with hexane, dried in vacuo to obtain 11a (53.29 g, 83%) as a pale yellow solid: 1H NMR (DMSO-d6) delta 7.78 (1H, dd, J = 6.4, 8.3 Hz), 7.89 (1H, dd, J = 5.9, 9.8 Hz); FAB-MS m/z 235, 237 [(M-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 327-51-5.

Reference:
Article; Negoro, Kenji; Yonetoku, Yasuhiro; Misawa-Mukai, Hana; Hamaguchi, Wataru; Maruyama, Tatsuya; Yoshida, Shigeru; Takeuchi, Makoto; Ohta, Mitsuaki; Bioorganic and Medicinal Chemistry; vol. 20; 17; (2012); p. 5235 – 5246;,
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The chemical industry reduces the impact on the environment during synthesis 445-02-3, name is 4-Bromo-2-(trifluoromethyl)aniline, I believe this compound will play a more active role in future production and life. 445-02-3

EXAMPLE 21 (E)-4-Cyclopentyl-2-[4-(5-methyl-tetrazol-1-yl)-3-trifluoromethyl-phenyl]-but-2-enoic acid thiazol-2-ylamide A solution of 2-(trifluoromethyl)-4-bromoaniline (4.8 g, 20 mmol) in dry tetrahydrofuran (20 mL) was cooled to 0 C. and then treated with acetic anhydride (8.2 g, 80 mmol). The reaction mixture was stirred at 0 C. for 10 min and then allowed to warm to 25 C. The reaction mixture was stirred at 25 C. for 2 h, at which time, thin layer chromatography analysis of the reaction mixture indicated the absence of starting material. The reaction mixture was then concentrated in vacuo. The crude residue precipitated from diethyl ether (50 mL) and hexanes (50 mL). The solid was collected by filtrated and washed with hexanes to afford N-(4-bromo-2-trifluoromethyl-phenyl)-acetamide (5.07 g, 90%) as an amorphous white solid: EI-HRMS m/e calcd for C9H7BrF3NO (M+) 281.8352, found 281.8348.

The chemical industry reduces the impact on the environment during synthesis 445-02-3. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Sidduri, Achyutharao; US2002/35266; (2002); A1;,
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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 586-61-8 as follows. 586-61-8

To fuming nitric acid (5 mL) cooled to 5 was added neat 4-bromoisopropylbenzene(1.0 g, 5.023 mmol) dropwise at such a rate that the reaction temperature remained below 10. The reaction was stirred for 2 hours at 5-10, quenched with ice (50 g), extracted with ethyl acetate (50 mL), and the organic extract was washed with water (2×25 mL) and brine (25 mL), then dried over magnesium sulfate. filtered and concentrated by rotary evaporation. The residue was purified by silica gel flash chromatography eluting with 5:95 ethyl acetate/hexanes to afford the title compound as a light yellow solid (1.03 g, 4.22 mmol, 84%). 1H NMR (300 MHz, CHLOROFORM-D) delta ppml.27 (d, J=6.99 Hz, 6 H) 2.75 – 3.23 (m, 1 H) 7.29 (dd, J=8.82, 2.21 Hz, 1 H) 7.63 (d, J=8.09 Hz, 1 H) 7.69 (d, J=2.21 Hz, 1 H); MS (DCI) m/z 261/263 (M+NH4)+.

According to the analysis of related databases, 586-61-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT LABORATORIES; WO2008/133753; (2008); A2;,
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55289-36-6, These common heterocyclic compound, 55289-36-6, name is 3-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.

Reference Production Example 8 (0631) A mixture of 25.0 g of 1-bromo-2-methyl-3-aminobenzene, 60.0 g of triphosgene, and 400 ml of toluene was stirred with heating under reflux for 3 hours. The reaction mixture allowed to cool was concentrated under reduced pressure to obtain 30.3 g of 1-bromo-3-isocyanato-2-methylbenzene (referred to as 8A). (0632) 1H-NMR (CDCl3) delta(ppm): 2.42 (3H, s), 7.00 (1H, dt, J=0.5, 8.0 Hz), 7.05 (1H, dd, J=1.7, 8.0 Hz), 7.39 (1H, dd, 1.5, 7.7 Hz).

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 55289-36-6.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; SHIODA, Takayuki; ARIMORI, Sadayuki; (149 pag.)US2016/159755; (2016); A1;,
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58971-11-2, Name is 3-Bromophenethylamine, 58971-11-2, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

A mixture of 4-iodobenzoic acid (10.0 g, 40.32 mmol) in thionyl chloride (40 mL, 40.32 mmol) was stirred at 80 C for 16 hours. The reaction mixture was concentrated to give4-iodobenzoyl chloride (10.7 g, 99%) as a white solid. To a solution of 2-(3-bromophenyl)ethylamine (6.0 g, 29.99 mmol) and triethylamine (20 mL, 149.94 mmol) in dichioromethane (100 mL) at 0 C was added 4-iodobenzoyl chloride prepared above (9.6 g, 35.99 mmol) portionwise. The resulting mixture was stirred at 25 C for 4 hours and was then diluted with DCM (500 mL). Water (100 mL) was added to the reaction mixture and twolayers were separated. The organic layer was dried over anhydrous sodium sulfate, and was concentrated to give the title compound as a white solid (12 g, 93%). ?H NMR (400 MHz, CDC13) oe 7.75 (d, J= 8.4 Hz, 2H), 7.42 – 7.36 (m, 3H), 7.22 – 7.09 (m, 2H), 6.15 (s, 1H), 3.69- 3.64 (m, 2H), 2.91 – 2.87 (m, 2H).

Statistics shows that 3-Bromophenethylamine is playing an increasingly important role. we look forward to future research findings about 58971-11-2.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; LABADIE, Sharada; LIANG, Jun; ORTWINE, Daniel Fred; WANG, Xiaojing; ZHANG, Birong; ZBIEG, Jason; VINOGRADOVA, Maia; WANG, Tao; (150 pag.)WO2017/174757; (2017); A1;,
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21524-34-5, name is 2-Bromo-1,3,5-triisopropylbenzene, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 21524-34-5

General procedure: vial with a screw cap and a silicon-coated rubber septum wasconnected to a vacuum/nitrogen manifold through a needle,and it was evacuated and refilled with nitrogen three times. Dimethylphenylsilyllithium (0.4 M in THF, 2.5 mL, 2.0 equiv)was added to the vial under nitrogen atmosphere. 1-Bromo-3,5-dimethylbenzene (93.5 mg, 0.51 mmol) was added to the vial,then stirred at 30 C. After 1 h, the reaction mixture was analyzedby GC to check completeness of the reaction. When thereaction was complete, H2O was added and the mixture wasextracted three times with Et2O. The organic layer was washedwith water and the combined organic layer was then dried overMgSO4 followed by filtration and evaporation. The crudeproduct was purified by silica-gel column chromatography with hexane eluent, then further purified by gel permeation chromatographyto give 3da in 63% isolated yield (76.5 mg, 0.318mmol).

Statistics shows that 21524-34-5 is playing an increasingly important role. we look forward to future research findings about 2-Bromo-1,3,5-triisopropylbenzene.

Reference:
Article; Yamamoto, Eiji; Ukigai, Satoshi; Ito, Hajime; Synlett; vol. 28; 18; (2017); p. 2460 – 2464;,
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Some common heterocyclic compound, 28342-75-8, name is 1,5-Dibromo-2,4-difluorobenzene, molecular formula is C6H2Br2F2, 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. 28342-75-8

100 g of intermediate 1-1, 186 g of intermediate 1-2, 203 g of potassium carbonate, 23.7 g of tetrabutylammonium bromide (TBAB) were added to a 2 L three-necked flask, and 800 ml of toluene, 200 ml of ethanol, and 200 ml of water were sequentially added. Nitrogen gas was introduced, stirred for 15 min, 2.1 g of tetrakis(triphenylphosphine)palladium was added, and the mixture was heated to 80 ¡ãC for refluxing for 8 h. TLC was used to monitor the reaction of the starting material to room temperature and filtered to remove insoluble.The impurities were separated, and the organic phase was washed with water until neutral. After drying over anhydrous sodium sulfate, the residue was purified by silica gel column to obtain 104.5 g of intermediate 1 in a yield of 89.3percent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 28342-75-8, its application will become more common.

Reference:
Patent; Xi’an Ruilian New Materials Co., Ltd.; Sun Jun; Zhang Hongke; Liu Kaipeng; Yang Dandan; Tian Mi; He Haixiao; Li Jiangnan; Wang Xiaowei; Liu Qianfeng; Gao Renxiao; (33 pag.)CN109535131; (2019); A;,
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