Bromides-buliding-blocks

22385-77-9, The chemical industry reduces the impact on the environment during synthesis 22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, I believe this compound will play a more active role in future production and life.

Preparation 13 ,5-Di-/er/-butylbenzaldehydeDissolve l-bromo-3,5-di-/er/-butylbenzene (5.00 g, 18.57 mmol) in THF (50 mL) under a nitrogen atmosphere. Cool to -78 C. Slowly add w-butyllithium (2.5 M in hexanes) (22.29 mL, 55.72 mmol) at -78 C. Stir at -78 C for about 30 min. Add DMF (4.31 mL, 55.72 mmol) dropwise. Warm the mixture to 0 C and stir for 2.5 h. Pour aqueous NH4CI (30 mL) into the mixture. Extract with EtOAc (3 x 20 mL). Dry the combined organic portions over a2S04; filter; collect the filtrate; and concentrate under reduced pressure. Purify the residue using flash chromatography eluting with a gradient of 0-10% EtO Ac/petroleum ether to afford the title compound (2.96 g, 73%) as a white solid. LC-ES/MS m/z 219 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-3,5-di-tert-butylbenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ELI LILLY AND COMPANY; BLEISCH, Thomas, John; COATES, David, Andrew; HUGHES, Norman, Earle; JONES, Scott, Alan; NORMAN, Bryan, Hurst; WO2013/66640; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

A common heterocyclic compound, 73918-56-6, name is 2-(4-Bromophenyl)ethanamine, molecular formula is C8H10BrN, 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. 73918-56-6.

2-(4-Bromophenyl)-ethylamine (13, 10.0g, 50mmol) and NaOH (3.0g, 75mmol) were dissolved in the mixture of dioxane (150mL) and H2O (150mL). The reaction mixture was cooled to 0C. The solution of di-tert-butyl dicarbonate (16.36g, 75mmol) in dioxane (72mL) was added dropwise to the reaction mixture, which was stirred at room temperature for 5.5h. Dioxane was removed in vacuo and the residue was extracted with ethyl acetate 3 times. The combined organic layer was washed with water and brine, and then dried over anhydrous Na2SO4. Filtration and removal of solvent provided the crude product, which was purified by Combiflash chromatography (5-10% of ethyl acetate in hexane). The title compound 5 (13.5g, 90.0%) was obtained as a white solid; mp 59-60C. 1H NMR (300MHz, chloroform-d): delta=7.42 (d, J=8.0Hz, 2H), 7.07 (d, J=8.0Hz, 2H), 4.51 (br. s, 1H), 3.40-3.27 (m, 2H), 2.75 (t, J=6.9Hz, 2H), 1.43 (s, 9H). MS (EI): m/z=300.1 (M++H).

The synthetic route of 2-(4-Bromophenyl)ethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Qiao, Chang-Jiang; Ali, Hamed I.; Ahn, Kwang H.; Kolluru, Srikanth; Kendall, Debra A.; Lu, Dai; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 517 – 529;,
Bromide – Wikipedia,
bromide – Wiktionary

583-70-0, 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 583-70-0 as follows.

Example 1; Isopropyl 2-(2,4-dimethylphenyl)benzenesulfonate (Compound 11); [0056] A solution of isopropyl 2-(4,4,5,5-tetramethyl-l,3-dioxolan-2- yl)benzenesulfonate (0.65 g, 2.0 mmol, 1.0 equiv) and l-bromo-2,4-dimethylbenzene (0.37 g, 2.1 mmol, 1.05 equiv) in toluene (15 mL) was degassed, and Pd(OAc)2 was added followed by tri(o-tolyl)phosphine, and 3 mL of a degassed 2N aqueous K2CO3 solution. The mixture was stirred at 800C for 20 hours and then water (10 mL) was added and extracted with EtOAc. The organic layer was washed with brine and dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (20:1 hexanes/EtOAc) to afford Compound 11. 1H NMR (500 MHz, CDCIa) 8.13 (dd, J = 8.1, 1.2 Hz, IH), 7.61 (ddd, J = 7.6, 7.6, 1.4 Hz, IH), 7.50 (ddd, J = 8.1, 7.6, 1.4 Hz, IH), 7.26 (dd, J = 7.5, 1.2 Hz, IH), 7.08-7.01 (m, 3H), 4.73- 4.65 (m, IH), 2.36 (s, 3H), 2.03 (s, 3H), 1.26 (d, J= 6.3 Hz, 3H), 1.15 (d, J= 6.3 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 583-70-0, and friends who are interested can also refer to it.

Reference:
Patent; PHARMACOPEIA, LLC; ZHI, Lin; PICKENS, Jason; VAN OEVEREN, Cornelius, A.; HENDERSON, Ian; WO2010/135350; (2010); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 626-40-4, name is 3,5-Dibromoaniline, A new synthetic method of this compound is introduced below., 626-40-4

2.51 g (10.0 mmol) of 3,5-dibromophenylamine, 4.48 g (22.0 mmol) of iodobenzene, 0.58 g (0.5 mmol) of Pd (PPh ) (Tetrakis (triphenylphosphine) palladium (0)) and 6.21 g (45.0 mmol) of K CO were mixed with THF (tetrahydrofuran) / H 0(2/1) After dissolving in 40 mL of the solution, the mixture was stirred at 80 C. for 5 hours. The reaction solution was cooled to room temperature, and thenextracted three times with 40 mL of water and 40 mL of diethyl ether. The organic layer thus obtained was dried over magnesium sulfate and the residue obtainedby evaporation of the solvent was separated and purified by silica gel column chromatography to obtain Intermediate I-4 (2.11 g, 86% yield). The resulting compound was confirmed by LC-MS.

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; Samsung Display Co., Ltd.; Kim Yeong-guk; Hwang Seok-hwan; Jeong Hye-jin; Park Jun-ha; Lee Eun-yeong; Im Jin-o; Han Sang-hyeon; Jeong Eun-jae; Kim Su-yeon; Lee Jong-hyeok; (64 pag.)KR102052070; (2019); B1;,
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bromide – Wiktionary

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.

The specific synthetic route of the compound is now provided:250ml of four bottles, in the atmosphere of nitrogen,0.01 mol of 2- (4-bromophenyl) -dibenzofuran, 0.025 mol of acridine,0.03 mol sodium tert-butoxide, 1 x 10-4 mol Pd2 (dba) 3, 1 x 10-4 mol tri-tert-butylphosphine,150ml toluene, heated reflux 24 hours, sampling point plate, the reaction is complete, natural cooling, filtration,The filtrate was steamed and passed through a silica gel column to give the target product with 99.0percent purity and 69.00percent yield.

The chemical industry reduces the impact on the environment during synthesis 4-(4-Bromophenyl)dibenzo[b,d]furan. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CECEP Wanrun Co., Ltd.; Li Chong; Xu Kai; Zhang Zhaochao; (37 pag.)CN107056758; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

A common heterocyclic compound, 68322-84-9, name is 2-Bromo-1-fluoro-4-(trifluoromethyl)benzene, molecular formula is C7H3BrF4, 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. 68322-84-9.

EXAMPLE 211 (+)-(4aR)-(10bR)-4-methyl-8-(2-fluoro-5-trifluoromethylphenyl)-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one STR229 A 15 mL round bottom flask was charged with (+)-(4aR)-(10bR)-4-methyl-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one-8-boronic acid (178 mg, 0.65 mmol), tetrakis(triphenylphosphine)palladium(0) (23 mg, 0.02 mmol), 3-bromo-4-fluorobenzotrifluoride (158 mg, 0.65 mmol), 0.65 mL of 2M aqueous sodium carbonate and 2 mL of THF, fitted with a reflux condenser, and the stirred mixture was heated at 80, under nitrogen, for 24 h. The mixture was cooled, diluted with ethyl acetate (75 mL) and washed with brine (2*25 mL). The combined organic extracts were dried over sodium sulfate, concentrated, and purified by silica gel chromatography (70% ethyl acetate/hexanes eluent) to give 113 mg (44%) of the title compound as an oil. FDMS: m/e =391. alpha[D]589 =+55.84 (c=0.34, chloroform)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-1-fluoro-4-(trifluoromethyl)benzene, its application will become more common.

Reference:
Patent; Eli Lilly and Company; US5578724; (1996); A;,
Bromide – Wikipedia,
bromide – Wiktionary

The chemical industry reduces the impact on the environment during synthesis 699-03-6, name is 1-(4-Bromophenyl)-N-methylmethanamine, I believe this compound will play a more active role in future production and life. 699-03-6

The prepared Formula-G was then dissolved in dichloromethane (1.8 L). Triethylamine (1.6 moles, 223.2 mL) was added at 5 C. A solution of methyl chloroformate (1.3 moles, 100.4 mL in dichloromethane (0.2 L) was slowly added, maintaining the temperature of the mixture between about 10 C and 14 C. The reaction solution was stirred at room temperature for 12 hours. Water was added to the reaction mass and the organic phase was separated and concentrated to afford a compound of Formula-E (wherein L=Br, P=methyl carbamate).

The chemical industry reduces the impact on the environment during synthesis 699-03-6. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MYLAN LABORATORIES LTD; JAYACHANDRA, Sureshbabu; SETHI, Madhuresh; KAUSHIK, Vipin Kumar; RAVI, Vijaya, Krishna; TELAGAMSETTY, Bhaskar Kumar; (44 pag.)WO2019/130229; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

608-30-0, 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. 608-30-0, name is 2,6-Dibromoaniline, This compound has unique chemical properties. The synthetic route is as follows.

(1) Preparation of 2,6-Bis(4-t-butylphenyl)aniline The same procedure as in Example 1(1) was used except that reaction was conducted by using 2,6-dibromoaniline (9.00 g, 35.6 mmol), Pd(PPh3)4 (5.0 g), and 4-t-butylphenyl boronic acid (19.0 g, 107 mmol). Yield 3.0 g. 1H NMR (CD2Cl2): delta 7.50 (d, 4H, Harom), 7.43 (d, 4H, Harom), 7.08 (d, 2H, Harom), 6.83 (t, 1H, Harom), 3.93 (s, 2H, NH2), 1.38 (s, 18H, t-Bu).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Razavi, Abbas; Marin, Vladimir; Lopez, Margarito; US2005/90385; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

The chemical industry reduces the impact on the environment during synthesis 156682-52-9, name is 1,4-Dibromo-2,3-difluorobenzene, I believe this compound will play a more active role in future production and life. 156682-52-9

To a solution of (S)-5-(hydroxymethyl)pyrrolidin-2-one (1.0 g, 8.7 mmol) in 1,4-dioxane (15 mL) at rt, were added 1,4-dibromo-2,3-difluorobenzene (2.4 g, 8.7 mmol), K3PO4 (3.7 g, 17 mmol) and, N,N-dimethylethylenediamine (0.15 g, 1.7 mmol). The reaction mixture was purged with nitrogen for 5 min and then charged with copper (I) iodide (0.17 g, 0.87 mmol). The reaction mixture was again purged with nitrogen for 3 min and heated at 95 C. for 12 h. The reaction mixture was cooled, filtered through a Celite pad and the filtrate was concentrated under reduced pressure. The crude compound was purified by column chromatography (3% MeOH-CHCl3) to yield Intermediate 28 (0.80 g, 2.6 mmol, 30% yield) as a yellowish solid. MS(ESI) m/z: 305.9 [M+H]+. 1H NMR (400 MHz, DMSO-d6) delta=7.59 (ddd, J=8.8, 7.0, 2.3 Hz, 1H), 7.24 (ddd, J=9.0, 7.0, 2.0 Hz, 1H), 4.80 (t, J=5.0 Hz, 1H), 4.20-4.04 (m, 1H), 3.37 (dd, J=5.0, 4.0 Hz, 2H), 2.56-2.45 (m, 1H), 2.43-2.35 (m, 1H), 2.25-2.18 (m, 1H), 2.07-1.95 (m, 1H).

The chemical industry reduces the impact on the environment during synthesis 156682-52-9. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Shirude, Pravin Sudhakar; Baligar, Vishweshwaraiah; Seshadri, Balaji; Chattopadhyay, Amit Kumar; Wurtz, Nicholas R.; Kick, Ellen K.; (91 pag.)US2019/270704; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding some certain compound to certain chemical reactions, such as: 626-40-4, name is 3,5-Dibromoaniline, 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 626-40-4. 626-40-4

1-Benzoyl-3-(3,5-dibromo-phenyl)-thiourea.To the solution of 3,5-dibromoaniline (65.0 g, 0.26 mol) in anhydrous acetone (1.6 L) was added benzoylisothiocyanate (46.4 g, 0.28 mol) and the reaction mixture was stirred at room temperature for 30 min. Acetone was distilled off and the crude residue was washed with hexane to obtain desired compound as yellow solid (96.5 g, 90 %).1H-NMR (400 MHz1 DMSO-d6): delta 7.56 (t, J= 7.60 Hz, 2H), 7.67 (t, J= 7.20 Hz, 1 H), 7.75 (s, 1 H), 7.96-7.98 (m, 4H), 11.76 (br s, 1 H) and 12.54 (br s, 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 3,5-Dibromoaniline.

Reference:
Patent; PROLYSIS LTD.; WO2007/148093; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary