Category: bromides-buliding-blocks

10016-52-1, A common compound: 10016-52-1, name is 2,8-Dibromodibenzo[b,d]furan, belongs to bromides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

In a nitrogen atmosphere, a flask containing 2,8-dibromodibenzo[b,d]furan (2.5 g), (10-phenylanthracen-9-yl) boronic acid (5.7 g), Pd-132 (0.27 g), tetrabutylammonium bromide (0.25 g), potassium carbonate (3.2 g), water (10 ml), and toluene (100 ml) was stirred at a reflux temperature for two hours. The reaction liquid was cooled to room temperature and subjected to liquid separation. The obtained organic layer was washed with water. This solution was decolorized using silica gel and concentrated under reduced pressure. The precipitated solid was washed with heptane to obtain compound (2A-201) (2.5 g). The structure of the compound thus obtained was identified by an NMR analysis. 1H-NMR (400 MHz, CDCl3):delta=8.06?8.05 (m,2H), 7.93?7.90 (m,2H), 7.77?7.70 (m,8H), 7.65?7.55 (m,8H), 7.55?7.47 (m,4H), 7.36?7.31 (m,8H).

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, 2,8-Dibromodibenzo[b,d]furan, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kwansei Gakuin Educational Foundation; JNC Corporation; HATAKEYAMA, Takuji; TAJIMA, Akio; BABA, Daisuke; FUJITA, Yukihiro; YAMAGA, Yuko; IMAI, Hiroyuki; (139 pag.)US2019/312207; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding some certain compound to certain chemical reactions, such as: 73918-56-6, name is 2-(4-Bromophenyl)ethanamine, 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 73918-56-6. 73918-56-6

EXAMPLE 63C 4-Bromo-(N-tert-butoxycarbonyl)phenethylamine 4-Bromophenethylamine and di-t-butyldicarbonate were subjected to the conditions described in Synthesis, 48, 1986 to provide the title compound. MS (DCI/NH3) m/e 319 (M+NH4)+.

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 2-(4-Bromophenyl)ethanamine.

Reference:
Patent; Abbott Laboratories; US6284796; (2001); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

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 73918-56-6 as follows. 73918-56-6

A solution of 4-bromophenylethyl amine (4.7 g, 23.5 mmol) and Et3N (6.5 mL, 47.0 mmol) in 100 mL of CH2Cl2 is cooled to -30 0C. Benzyl chloroformate (4 ml, 28.2 mmol) is added drop-wise. The reaction mixture is allowed to warm up to 23 0C slowly and stirred for 5 h. The reaction mixture is poured into crushed ice- water and extracted with CH2Cl2 (100 mL x 3). The organic layer is washed with water, brine, and dried over Na2SO4, and concentrated in vacuo. The crude product is purified by passing through a silica gel pad and eluting with 5% MeOH in CH2Cl2 and then 1 :2 EtOAc-hexanes to give the desired intermediate 1.1 (7.5 g, 97%) as a white solid.

According to the analysis of related databases, 73918-56-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2009/52078; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

937046-98-5, Name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, 937046-98-5, 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.

In a Bohdan Miniblock N-(3-phenylbutyl)-3-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)benzamide (15 mg, 0.040 mmol) and 7-bromopyrrolo[2,1- f][1,2,4]triazin-4-amine (16.9 mg, 0.079 mmol) were dissolved in DMF (400 mul). To the vial was added PdCl2(dppf)-CH2Cl2 adduct (3.23 mg, 3.95 mumol), followed by tripotassium phosphate (59.3 mul, 0.119 mmol). The reaction mixture was capped, degassed and purged with N2. After stirring 1 h at 100 C, the mixture was cooled to rt. The crude material was purified via preparative LC/MS with the following conditions: Column: XBridge C18, 19 x 200 mm, 5-mum particles; Mobile Phase A: 5:95 acetonitrile: water with 10-mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile: water with 10- mM ammonium acetate; Gradient: 20-60% B over 20 min, then a 5-minute hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation to yield the final product (6.8 mg, 17.6 mumol, 44 %). (0438) MS ESI m/z 386.2 (M+H) (0439) 1H NMR (500 MHz, DMSO-d6) delta 8.56 – 8.47 (m, 1H), 8.41 (s, 1H), 8.24 (br d, J=7.7 Hz, 1H), 7.95 (s, 1H), 7.92 – 7.76 (m, 2H), 7.73 (br d, J=7.7 Hz, 1H), 7.53 (t, J=7.8 Hz, 1H), 7.36 – 7.24 (m, 4H), 7.22 – 7.16 (m, 1H), 7.10 (d, J=4.5 Hz, 1H), 7.04 (d, J=4.5 Hz, 1H), 3.23 (dq, J=13.2, 6.5 Hz, 1H), 3.18 – 3.09 (m, 1H), 2.85 – 2.75 (m, 1H), 1.84 (q, J=7.3 Hz, 2H), 1.24 (br d, J=6.8 Hz, 3H).

Statistics shows that 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine is playing an increasingly important role. we look forward to future research findings about 937046-98-5.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WATTERSON, Scott Hunter; ANDAPPAN MURUGAIAH SUBBAIAH, Murugaiah; DZIERBA, Carolyn Diane; GONG, Hua; GUERNON, Jason M.; GUO, Junqing; HART, Amy C.; LUO, Guanglin; MACOR, John E.; PITTS, William J.; SHI, Jianliang; VENABLES, Brian Lee; WEIGELT, Carolyn A.; WU, Yong-Jin; ZHENG, Zhizhen Barbara; SIT, Sing-Yuen; CHEN, Jie; (810 pag.)WO2019/147782; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

A common heterocyclic compound, 55289-36-6, name is 3-Bromo-2-methylaniline, molecular formula is C7H8BrN, 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. 55289-36-6.

Example lOld Methyl 3-((3-Bromo-2-methylphenylamino)methyl)-5-ieri- xylate lOldA 250-mL single-necked round-bottomed flask equipped with a magnetic stirrer was purged with nitrogen and charged with 101c (1.09 g, 4.68 mmol), 3-bromo-2-methyl-aniline (2.61 g, 14.0 mmol) and acetonitrile (25 mL). Cesium carbonate (1.67 g, 5.15 mmol) was added and the mixture was stirred at room temperature for 16 h. The reaction mixture was then concentrated under reduced pressure. Purification of the resulting residue by column chromatography afforded a 70% yield (1.30 g) of lOld as a yellow oil: ]H NMR (300 MHz, CDCI3) delta 6.92 (m, 2H), 6.85 (s, 1H), 6.57 (dd, 1H, / = 4.8, 2.1 Hz), 4.60 (s, 2H), 3.86 (s, 3H), 2.29 (s, 3H), 1.37 (s, 9H); MS (ESI+) mJz 396.2 (M+H).

The synthetic route of 3-Bromo-2-methylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD CONNECTICUT, INC.; GENENTECH, INC.; CURRIE, Kevin S.; WANG, Xiaojing; YOUNG, Wendy, B.; WO2012/30990; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 1073-39-8

To a mixture of 3-bromobicyclo[4.2.0]octa-1,3,5-triene (80 g, 437.05 mmol, 1.05 equiv) in THF (800 mL) was added n-BuLi (2.5M in hexane, 180 mL, 1.10 equiv) dropwise at -78C, and the reaction mixture was stirred at – 78C for 30 min. 5-Bromo-2-methoxybenzaldehyde (89.5 g, 416.19 mmol, 1.00 equiv) in THF (800 mL) was then added to the solution dropwise at -78C. The reaction mixture was stirred at -78C for 2 h. NH4CI/H20 was added and the mixture was extracted with EtOAc thrice. The combined extracts were washed with brine and dried over Na2S04, then concentrated and purified by chromatography on silica gel (10: 1 PE/EA) to yield (5-bromo-2- methoxyphenyl)(1,2-dihydrocyclobutabenzen-4-yl)methanol as a colorless oil.

The synthetic route of 1073-39-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; GAUL, Micheal; KUO, Gee-Hong; XU, Guozhang; LIANG, Yin; (218 pag.)WO2018/89449; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

2270-59-9, name is 5-Bromo-2-methylpent-2-ene, 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. 2270-59-9

A dry Schlenk tube equipped with a stirring bar was charged with dimethyl oxalate(0.5 g, 4.2 mmol, 1.0 equiv.) and then the flask was evacuated and refilled with N2 (x3). Dry THF (0.7 M) was added and the mixture was cooled to -78 C. A freshlyprepared solution of 4-methylpent-3-en-1-yl)magnesium bromide (1.05 equiv.) wasadded by dropwise [Grignard preparation: a dry Schlenck tube equipped with astirring bar was charged with Mg turnings (1.1 equiv.) and then the flask wasevacuated and refilled with N2 (x 3). The minimum amount of THF was added andthen 5-bromo-2-methylpent-2-ene (0.3 equiv.) was added neat. Once the Grignardreaction started the remaining 5-bromo-2-methylpent-2-ene (0.75 equiv.) were addedas a solution in THF (2 M). The corresponding mixture was stirred for 1 additional hour]. The mixture was allowed to warm to room temperature overnight. NH4Cl was added and the mixture was diluted with Et2O. The layers were separated and the organic layer was dried (MgSO4), filtered and evaporated. Purification by columnchromatography on silica gel, eluting with petrol-Et2O 95:5, gave S7 (0.2 g, 25%) asan oil. 1H NMR (400 MHz, CDCl3) delta 5.07 (1H, t, J = 7.2 Hz), 3.86 (3H, s), 2.87 (2H,t, J = 7.3 Hz), 2.32 (2H, q, J = 7.3 Hz), 1.67 (3H, s), 1.62 (3H, s); 13C NMR (101 MHz, CDCl3) delta 194.1, 161.6, 133.7, 121.9, 53.0, 39.7, 25.8, 21.9, 17.8; HRMS (ESI): Found MNH4+ 188.1280 C9H18O3N requires 188.1281.

Statistics shows that 2270-59-9 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2-methylpent-2-ene.

Reference:
Article; Davies, Jacob; Angelini, Lucrezia; Alkhalifah, Mohammed A.; Sanz, Laia Malet; Sheikh, Nadeem S.; Leonori, Daniele; Synthesis; vol. 50; 4; (2018); p. 821 – 830;,
Bromide – Wikipedia,
bromide – Wiktionary

327-51-5, 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. 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a 1.0 M solution (tetrahydrofuran 1:1 toluene) of 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex (200 cm3, 200 mmol) at -30 C. under inert atmosphere is added drop-wise a solution of 1,4-dibromo-2,5-difluoro-benzene (23.6 g, 86.8 mmol) in anhydrous tetrahydrofuran (150 cm3) over 30 minutes. After addition, the reaction mixture is stirred at -30 C. for 7 hours before ethyl chloroformate (22.6 g, 208 mmol) is added in one go. The mixture is then allowed to warm to 23 C. over 17 hours. Aqueous hydrochloric acid (1.0 M, 500 cm3) is added and the mixture stirred at 23 C. for 30 minutes. The product is extracted with diethyl ether (3*100 cm3). The combined organics are dried over anhydrous magnesium sulfate, filtered and the solvent removed in vacuo. The crude product is triturated with n-pentane to form a suspension. The product is filtered and washed with cold acetone, collected and dried under vacuum to give 2,5-dibromo-3,6-difluoro-terephthalic acid diethyl ester (12.0 g, 33%) as a white solid. 1H-NMR (300 MHz, CDCl3) 1.42 (6H, m, CH3), 4.49 (4H, q, CH3) 19F-NMR 108.72 (2F, s, CF).

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

Reference:
Patent; Merck Patent GmbH; D’LAVARI, Mansoor; MITCHELL, William; WANG, Changsheng; SPARROWE, David; (67 pag.)US2017/117477; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

393-36-2, These common heterocyclic compound, 393-36-2, name is 4-Bromo-3-(trifluoromethyl)aniline, 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.

4-Bromo-3-(trifluoromethyl)aniline was converted into 4-bromo-3-(trifluoromethyl)phenyl isocyanate according to Method B1. According to Method C1a, 4-bromo-3-(trifluoromethyl)phenyl isocyanate was reacted with 4-(2-(N,N-dimethylcarbamoyl)-4-pyridyloxy)aniline to afford the urea. Entry 92: 4-Chloro-N-methylpyridinecarboxamide was synthesised as described in Method A2, Step 3b.

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 393-36-2.

Reference:
Patent; Riedl, Bernd; Dumas, Jacques; Khire, Uday; Lowinger, Timothy B.; Scott, William J.; Smith, Roger A.; Wood, Jill E.; Monahan, Mary-Katherine; Natero, Reina; Renick, Joel; Sibley, Robert N.; US2001/11135; (2001); A1;; ; Patent; BAYER CORPORATION; US2003/181442; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

A common heterocyclic compound, 553-94-6, name is 2,5-Dimethylbromobenzene, molecular formula is C8H9Br, 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. 553-94-6.

1) Add 1 mol of 2-bromo-p-xylene or chloroacetyl chloride to the reaction kettle.The catalyst and DMSO were heated to 100 C under stirring for 5 h.Then a mixture of sodium sulfite and water was added dropwise to control the dropping time to 45 min.After the completion of the dropwise addition, the reaction temperature was raised to 135 C, and the reaction was continued for 7.5 h; The ratio of 2-bromo-p-xylene to chloroacetyl chloride is 1:1.14,The ratio of 2-bromo-p-xylene to catalyst is 1:0.07, and the ratio of 2-bromo-p-xylene to DMSO is 1g: 13ml.The ratio of 2-bromo-p-xylene to sodium sulfite was 1:1.18, and the ratio of sodium sulfite to water was 1:4.5. The preparation process of the catalyst is: Mix ruthenium oxide and 10% palladium carbon in a weight ratio of 1:20. Then soaked in 4% concentration of hydrochloric acid for 6 minutes,Then, a solid was obtained by filtration, and the solid was washed and then placed at 280 C for 2.5 h to obtain a catalyst. 2) cooling the system, filtering to remove insoluble matter to obtain a filtrate, and adding the filtrate to about 5 volumes of water.Then, the filtrate is added twice the volume of toluene, and the layer is allowed to stand, and the organic phase is washed with water.After drying with anhydrous sodium sulfate,Concentration gave the product in a molar yield of 98.1% and a HPLC purity of 97.5%.

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

Reference:
Patent; Shandong Nong Pharmaceutical Xue Institute; Jinan Kehai Co., Ltd.; Fu Hongxin; Yang Chaohui; Wang Ling; (6 pag.)CN109369378; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary