Category: bromides-buliding-blocks

Application of 4549-33-1, 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 4549-33-1 as follows.

DIEA (259 mg, 2 mmol) and 1,9-dibromoctane (286 mg,1 mmol) were added to the mixture whichincluded compound 1a (508 mg, 2 mmol) in toluene/ethanol (EtOH) (1:1) (60 mL), followed by refluxfor 48 h. The solvent was removed under vacuum. The process of this reaction was controlled byLC-MS and TLC. For TLC control and purification, the DCM/MeOH (7/1) system was used. Neutralalumina oxide was used to purify the product (yield 50%). LC-MS: [M + H]+ = 633. 1H NMR (500 MHz, MeOD): delta = 1.31(m, 2H, CH2), 1.41 (m, 12H, 6xCH2), 2.20 (m, 4H, 2xCH2),3.04 (m, 4H, 2xNHCH2), 3.13 (m, 4H, 2xNHCH2), 3.89 (d, J = 10.3 Hz, 4H, 2xNCH2) 7.86 (t, J = 7.8 Hz,4H, ArH), 8.41 (d, J = 8.1 Hz, 4H, ArH), 8.60 (d, J = 7.1 Hz, 4H, ArH) ppm.13C NMR (125 MHz, CDCl3): delta = 22.3 (CH2), 23,2 (CH2), 26,5 (CH2), 27,1 (CH2), 28.7 (CH2),37.9 (CH2), 46.5 (CH2), 48,6 (CH2), 122.3 (Caro), 127.2 (CaroH), 127.3 (Caro), 130.7 (CaroH), 131.3 (Caro),134.3 (CaroH), 163.5 (C=O) ppm.

According to the analysis of related databases, 4549-33-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Keskin, Elif; Ucisik, Mehmet Hikmet; Sucu, Bilgesu Onur; Guzel, Mustafa; Molecules; vol. 24; 24; (2019);,
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Reference of 7745-91-7, 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. 7745-91-7, name is 3-Bromo-4-methylaniline, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of Compound 1 (5 g, 26.87 mmol, 1 eq) in acetone (50 mL) was added benzoyl isothiocyanate (4.39 g 26.87 mmol, 3.62 mL, 1 eq) in acetone (10 mL) dropwise at 60 C. The mixture was refluxed at 60 C. for 4 hr. TLC (Petroleum ether/Ethyl acetate=5/1) showed Compound 1 was consumed and a main spot. The mixture was concentrated. The residue was purified by triturated with Petroleum ether (60 mL) and Ethyl acetate (6 mL). Compound 2 (8.77 g, 25.11 mmol, 93% yield) was obtained as white solid. 1H NMR (400 MHz, CDCl3) delta=12.58-12.23 (m, 1H), 9.20-9.02 (m, 1H), 8.01-7.85 (m, 3H), 7.72-7.64 (m, 1H), 7.60-7.54 (m, 3H), 7.30 (s, 1H), 2.46-2.40 (m, 3H).

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-4-methylaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; 1ST Biotherapeutics, Inc.; LEE, Jinhwa; KIM, Jae Eun; JO, Suyeon; LEE, Gwibin; LIM, Keonseung; PARK, A Yeong; KIM, Misoon; JUNG, Gyooseung; LIM, Seung Mook; LEE, Minwoo; YANG, Heekyoung; KIM, Hyonam; KIM, Hyeongjun; LI, Wanjun; FAN, Mingzhu; (82 pag.)US2019/100500; (2019); A1;,
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Application of 3814-30-0, The chemical industry reduces the impact on the environment during synthesis 3814-30-0, name is (Bromomethyl)cyclopentane, I believe this compound will play a more active role in future production and life.

Under the protection of nitrogen, the future nalidamine derivative (0.1 mmol),Sodium metabisulfite (0.2mmol, 2.0equiv.), Tin powder (0.3mmol, 3.0equiv.),1,1′-bis (diphenylphosphino) ferrocene palladium dichloride (0.01mmol, 10mol%), 1,1′-bis (diphenylphosphine) ferrocene (0.02mmol, 20mol%) , Dipotassium hydrogen phosphate trihydrate (0.2 mmol, 2.0 equiv.), And tetrabutylammonium bromide (0.15 mmol, 1.5 equiv.) Were added to a reaction tube containing magnetons,After evacuation of nitrogen for three times, bromomethylcyclopentane (0.3 mmol, 3.0 equiv.) And DMSO (1.0 mL) were added, and the reaction system was heated to 100 C for 10 hours.After detecting the complete conversion of aryl iodide on the plate, the reaction system was cooled to room temperature, diluted with water, and extracted with ethyl acetate (10 mL * 3), dried over anhydrous sodium sulfate, filtered, concentrated, and purified by column chromatography. The desired product 3bd (77%).

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, (Bromomethyl)cyclopentane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; East China Normal University; Jiang Xuefeng; Meng Yingying; Wang Ming; (40 pag.)CN110563619; (2019); A;,
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Reference of 460-00-4,Some common heterocyclic compound, 460-00-4, name is 1-Bromo-4-fluorobenzene, molecular formula is C6H4BrF, 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.

30 g (0.26 mol) of indole in a 250 mL round bottom flaskAnd 44.8 g (0.26 mol) of 4-fluorobromobenzene,Potassium fluorine 29.8 g (0.51 mol),1.35 g (5 mmol) of 18-crown-6 and 300 ml of dimethyl sulfoxide were added and refluxed for 24 hours.After the reaction was completed, the reaction mixture was cooled to room temperature, extracted, and the organic layer was concentrated under reduced pressure, separated by column chromatography using hexane and ethyl acetate, and dried to obtain 47.6 g (68.3%) of the compound represented by Chemical Formula 11-a.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-4-fluorobenzene, its application will become more common.

Reference:
Patent; SFC Ltd.; Che Jong-tae; Jeong Seong-uk; Park Ji-hui; Ryu Yeon-gwon; (47 pag.)KR101996648; (2019); B1;,
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Related Products of 114078-88-5, A common heterocyclic compound, 114078-88-5, name is 5-Bromo-1,2,3-triazine, molecular formula is C3H2BrN3, 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.

In a 10 mL dry sealed reaction tube, add 5-bromo-1,2,3-triazine 1a (15.9 mg, 0.10 mmol), DBN (37.3 mg, 0.30 mmol) in sequenceAnd 2-acetonitrile pyridine 6b (23.6 mg, 0.20 mmol). After nitrogen substitution three times, the solvent 1,4-dioxane (1.0 mL) was added, and the sealed reaction tube was placed at 70 C. for 4 h. The reaction was monitored by TLC. After the reaction was completed, it was extracted with dichloromethane (3 * 10 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo to obtain the target product 27c. For the single crystal structure, see FIG. 1.

The synthetic route of 114078-88-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chongqing University; Li Baosheng; Luo Han; Zhang Yuan; An Jiaoyu; Xu Mingchuan; Lu Qixing; Tang Zongyuan; Li Shanshan; (16 pag.)CN111004284; (2020); A;,
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Electric Literature of 2576-47-8, 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 2576-47-8 as follows.

General procedure: The different arylsulfonyl chloride 2a-s (4 mmol) and 3-bromopropylamine hydrobromide (3) (4.6mmol) or 2-bromoethylamine hydrobromide (4) (4.6 mmol) were suspended in anhydrous DCM (14 mL)under nitrogen atmosphere. The reaction mixture was cooled to 0C in an ice-bath and then treateddropwise with triethylamine (1.34 mL, 9.6 mmol) over a period of 10 min. The reaction mixture wasstirred for 10 min under ice-cooling, then diluted with DCM (50 mL) and washed with 2M hydrochloricacid solution (2 x 60 mL) and brine (2 x 60 mL). The organic solvent was evaporated at reduced pressureafter drying over MgSO4.

According to the analysis of related databases, 2576-47-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Bassetto, Marcella; Leyssen, Pieter; Neyts, Johan; Yerukhimovich, Mark M.; Frick, David N.; Courtney-Smith, Matthew; Brancale, Andrea; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 1115 – 1131;,
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Electric Literature of 58534-95-5, 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 58534-95-5 as follows.

3-Bromo-2-fluoroaniline (10 g, 52.63 mmol) was dissolved in DCM (100 mL) under nitrogen atmosphere. Dry pyridine was added (6 mL, 73.68 mmol), followed by 2,5-difluorobenzenesulfonyl chloride (7.08 mL, 52.63 mmol) and the mixture was stirred at r.t. for 2 h. It was then diluted with DCM and washed with aqueous 0.5 N HCI (3 x 80 mL) and brine. The organic layer was dried over Na2S04 and evaporated to dryness. The solid was taken up with diethyl ether and stirred for 30 min. It was then filtered and dried at 40C under reduced pressure to give 17.8 g of A/-(3-bromo-2- fluoro-phenyl)-2,5-difluoro-benzenesulfonamide as a pale yellow solid (92%).HPLC: Rt: 6.28 min1H NMR (401 MHz, DMSO-d6) delta ppm 10.86 (s, 1 H), 7.50 – 7.73 (m, 4 H), 7.23 – 7.31 (m, 1 H), 7.12 (dt, J = 1.3, 8.1 Hz, 1 H)

According to the analysis of related databases, 58534-95-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.r.l.; PULICI, Maurizio; TRAQUANDI, Gabriella; MARCHIONNI, Chiara; SCOLARO, Alessandra; COLOMBO, Nicoletta; WO2012/113774; (2012); A1;,
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Application of 393-36-2,Some common heterocyclic compound, 393-36-2, name is 4-Bromo-3-(trifluoromethyl)aniline, molecular formula is C7H5BrF3N, 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. 6-Bromo-3-(ethyl oxalamido)benzotrifluoride To a stirred solution of 3-amino-6-bromobenzotrifluoride (2.40 g, 10.00 mmol, Aldrich) in dried THF (10 mL) and triethylamine (1 mL) in an ice bath was dropwise added ethyl oxalyl chloride (1.7 mL, 16 mmol, Aldrich). The resulting yellow suspension was stirred at 25 C. for 3 h and it was poured into ice water (50 mL). The precipitate was collected by filtration to give 3.304 g (97%) of crude 6-bromo-3-(ethyl oxalamido)benzotrifluoride. Crystallization from ethanol/water gave 2.95 g (85%) of pure compound. 1 H NMR (CDCl3): delta1.434 (t, 3H, J=6.9 Hz); 4.432 (q, 2H, J=6.9 Hz), 7.715 (d, 1H, J=8.7 Hz); 7.802 (d, 1H, J=8.7 Hz); 7.946 (d, 1H, J=1.8 Hz), 8.991 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-3-(trifluoromethyl)aniline, its application will become more common.

Reference:
Patent; The State of Oregon, acting by and through The Oregon State Board of Higher Education, acting for and on behalf of The Oregon Health Sciences University; The University of Oregon; The Regents of the University of California; US5514680; (1996); A;,
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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 129316-09-2 as follows. name: 1,3-Dibromo-5-(tert-butyl)benzene

Step 1 1-Bromo-3-(tert-butyl)-5-methoxybenzene (14a) To a solution of 1,3-dibromo-5-tert-butylbenzene (289 mg, 1 mmol) in 20 mL DMF were added NaOMe (2 eq) and Cul (0.03 eq). The mixture was stirred at 80C for 3 h and then was poured into water and extracted with EA. The organic layers were washed with brine and dried over anhydrous Na2SO4. After filtration, the filtrate was evaporated to give compound 14a as solid (200 mg, 82%).

According to the analysis of related databases, 129316-09-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Phenex Pharmaceuticals AG; EP2511263; (2012); A1;,
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Related Products of 955959-84-9, The chemical industry reduces the impact on the environment during synthesis 955959-84-9, name is 4-(4-Bromophenyl)dibenzo[b,d]furan, I believe this compound will play a more active role in future production and life.

Intermediate M-1 15g (46.4mmol) in a round bottom flask and 9,9-Dimethyl-9H-fluoren-2-ylamine 4.8g (23.2mmol),sodium-t- butoxide 6.7g (69.6mmol) ofIt was dissolved in toluene into a 185ml. Here Pd (dba) 2 0.53g (0.928mmol) and tri-tert-butylphosphine was placed to 0.38g (1.86mmol) in turn and the mixture was stirred under reflux for 4 hours under a nitrogen atmosphere. After completion of the reaction and then extracted with toluene the organic layer was dried and distilled over magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The product n- hexane / dichloromethane (8: 2 by volume) to give compound 8 as a purification by a silica gel column chromatography as a white solid 14.4g (90percent yield).

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, 4-(4-Bromophenyl)dibenzo[b,d]furan, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SAMSUNG SDI CO., LTD.; JANG, YU NA; HONG, JIN SEOK; KIM, YOUNG KWON; YU, EUN SUN; KIM, CHANG WOO; KIM, HUN; MIN, SOO HYUN; CHO, PYEONG SEOK; (38 pag.)KR2016/12846; (2016); A;,
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