Bromides-buliding-blocks

Reference of 22364-25-6,Some common heterocyclic compound, 22364-25-6, name is 4-Bromo-2,3-dimethylaniline, 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.

EXAMPLE 26 Preparation of 2,3-Dimethyl-4-methylthiobromobenzene 603 g (5.85 mol) of tert-butyl nitrite and 375 g of copper powder (5.9 mol) are initially charged in 3000 ml of dimethyl disulfide, and 761 g (3.75 mol) of 4-bromo-2,3-dimethylaniline are added dropwise at from 50 to 58 C. The mixture is subsequently stirred at from 75 to 80 C. for 9 hours. For work-up, the mixture is cooled, the residue is filtered off and the filtrate is washed with saturated aqueous NaHCO3 solution. For purification of the product, the organic phase is separated by distillation. Initially, the excess dimethyl disulfide is separated off at atmospheric pressure. 1870 g of dimethyl disulfide (purity>97% according to GC) are recovered. The residue is subsequently subjected to fractional distillation under reduced pressure (0.1 mbar). Yield: 523 g (60%), purity according to GC 99%.

The synthetic route of 22364-25-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF Aktiengesellschaft; US6469176; (2002); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 58458-10-9, name is 3-Amino-2-bromobenzotrifluoride, 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. category: bromides-buliding-blocks

An ice-cold solution of NaNO2 (0.15 g) in water (0.5 mL) is added to a mixture of 2-bromo-3-trifluoromethyl-aniline (0.48 g), concentrated H2SO4 (2 mL), and water (1.8 mL) at ca. 5 C. The mixture is stirred in the cooling bath for 20 min and then poured into a solution of KI (0.56 g) and I2 (0.56 g) in water (0.5 mL). After gas evolution ceases, the mixture is heated to 40 C. and stirred at this temperature for 1 h. The mixture is cooled to room temperature and aqueous Na2SO3 solution is added. The resulting mixture is extracted with ethyl acetate, and the combined extracts are dried (Na2SO4) and concentrated. The solvent is evaporated and the residue is chromatographed (cyclohexane/ethyl acetate 95:5?90:10) to give the title compound.

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ECKHARDT, Matthias; US2014/221349; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 393-36-2, 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 393-36-2 as follows.

Example 89 [5-BROMO-6-TRIFLUOROMETHYL-2- [4- (3-TRIFLUOROMETHYL-PYRIDIN-2-YL)-PIPERAZIN-1-YL]-] 1H-benzoimidazole. (a) [N- [4-BROMO-3- (TRIFLUOROMETHYL)] phenyl] acetamide. A mixture [OF 4-BROMO-3- (TRIFLUOROMETHYL)] phenylamine (7.2 g, 30 mmol, Aldrich) and acetic anhydride (29 mL) was stirred at room temperature for 16 h. The reaction mixture was evaporated in vacuo to give the title product as a white solid which was used in the next step without additional purification. MS (ESI, pos. ion) [M/Z] : [484.] 0 (M+1).

According to the analysis of related databases, 393-36-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; WO2004/35549; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 2862-39-7, name is 2-Bromo-N,N-dimethylethanamine hydrobromide, belongs to bromides-buliding-blocks compound, 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 2862-39-7, Formula: C4H11Br2N

A mixture of 4- (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) -1H-pyrazole (1.5 g, 7.7 mmol) , 2-bromo-N, N-dimethylethanamine hydrobromide (4 g, 20 mmol) and Cs2CO3(9 g, 17.6 mmol) in DMF (15 mL) was stirred at 70 overnight. The reaction mixture was concentrated to remove DMF. The residue was diluted with water (20 mL) . The resulting mixture was extracted with DCM (30 mL ¡Á 3) . The combined organic layers were dried over anhydrous Na2SO4and concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with DCM/MeOH (v/v) 25/1 to give a white solid product (0.5 g, 20) .[1634]MS (ESI, pos. ion) m/z: 266.1 [M+1]+.

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-Bromo-N,N-dimethylethanamine hydrobromide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Bing; ZHANG, Yingjun; CHENG, Changchung; HUANG, Jiuzhong; BAI, Shun; REN, Xingye; LI, Zhi; ZHOU, Youbai; (368 pag.)WO2016/615; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 65896-11-9, 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. 65896-11-9, name is 2-Bromo-6-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 5,8-dimethoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalene-6-carbaldehyde 1 (0.23g, 0.97mmol), 2-bromo-6-fluoroaniline 9c (1 equiv, 0.18g, 0.97mmol), NaCNBH3 (2.5 equiv, 0.15g, 2.4mmol) and acetic acid (2 equiv, 0.12g, 1.9mmol) in iso-propanol (20mL) was stirred at room temperature for seven days. After this time, a saturated aqueous solution of Na2CO3 (15mL) was added and an extraction with EtOAc was performed (3¡Á15mL). After drying of the combined organic phases (MgSO4), filtration and evaporation, crude aniline 10c was obtained, which was purified by reverse phase automated flash chromatography (0.080g, 0.19mmol). 2-Bromo-N-[(5,8-dimethoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalen-6-yl)methyl]-6-fluoroaniline 10c. Pale yellow oil. Gradient used for purification: during 3 CV: 40% CH3CN, during 30 CV: 40 -> 100% CH3CN, during 3 CV: 100% CH3CN. Yield 20%. 1H NMR (400MHz, CDCl3): delta 1.17-1.28 (2H, m), 1.48 (1H, ddd, J=8.7Hz, 1.4Hz, 1.4Hz), 1.69-1.72 (1H, m), 1.86-1.98 (2H, m), 3.55-3.57 (1H, m), 3.62-3.64 (1H, m), 3.76 (3H, s), 3.86 (3H, s), 4.38 (1H, br s), 4.47 (2H, d, J=4.4Hz), 6.61 (1H, ddd, J=8.2Hz, 8.1Hz, JH,F=4.9Hz), 6.95 (1H, ddd, JH,F=12.4Hz, J=8.2Hz, 1.4Hz), 7.22 (1H, ddd, J=8.1Hz, 1.4Hz, 1.3Hz). 13C NMR (100.6MHz, ref=CDCl3): delta 26.6, 27.1, 39.7, 41.5, 46.7 (d, J=9.6Hz), 49.1, 56.0, 61.5, 110.2, 113.9 (d, J=5.5Hz), 116.0 (d, J=21.3Hz), 119.6 (d, J=8.5Hz), 128.2 (d, J=3.1Hz), 129.5, 135.4 (d, J=12.0Hz), 136.5, 140.3, 146.3, 148.9, 153.4 (d, J=245.0Hz). 19F NMR (376.5MHz, CDCl3, ref=CFCl3): delta-124.10 (1F, dd, JH,F=12.4Hz, 4.9Hz). MS (ES+): m/z (%): 217 (100).

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-6-fluoroaniline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Cappoen, Davie; Torfs, Eveline; Meiresonne, Tamara; Claes, Pieter; Semina, Elena; Holvoet, Francis; de Macedo, Maira Bidart; Cools, Freya; Piller, Tatiana; Matheeussen, An; Van Calster, Kevin; Caljon, Guy; Delputte, Peter; Maes, Louis; Neyrolles, Olivier; De Kimpe, Norbert; Mangelinckx, Sven; Cos, Paul; European Journal of Medicinal Chemistry; vol. 181; (2019);,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 112734-22-2, 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. 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of (4-bromo-2-fluorophenyl) methanamine (2.5 g, 12 mmol) in DCM (50 mL) at 0 C was added di-terf-butyl dicarbonate (4.01 g, 18 mmol) and triethylamine (2.6 mL, 18 mmol). The mixture was allowed to warm to room temperature and stirred for 2h. Water was added (50 mL) and the layers were separated. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuum. The crude product was purified by flash silica column chromatography (heptane:ethyl acetate) (1 :0 to 4:1 ) to afford the title compound as a colorless oil. (2.7 g, 71 %).1 H NMR (400 MHz, DMSO-d6) delta ppm 7.21 -7.26 (m, 3 H), 4.90 (br s, H), 4.27-4.33 (m, 2 H), 1 .44 (s, 9 H).

The chemical industry reduces the impact on the environment during synthesis (4-Bromo-2-fluorophenyl)methanamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; EVOLVA SA; HEIM, Jutta; SCHNEIDER, Peter; ROUSSEL, Patrick; MILLIGAN, Daniel; WO2012/104305; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, belongs to bromides-buliding-blocks compound, 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 22385-77-9, HPLC of Formula: C14H21Br

2-(3,5-Di-t-butylphenyl)benz[f]indene (Ligand J) Benz[f]indene (10.8 g, 0.065 mole) was dissolved in 100 mL of dimethylformamide. 1-Bromo-3,5-di-t-butylbenzene (14 g, 0.052 mole) was added along with palladium acetate (0.3 g), tri-o-tolylphosphine (0.8 g), and triethyl amine (11.0 g). The solution was heated to 60 C for 3 days. The solution was cooled and washed with 1 N HCl and by saturated sodium bicarbonate. The product was found to be difficult to separate from the residual tri-o-tolylphosphine. After purifying by passing through silica with hexanes three times, and recrystallization from ethanol, followed by three recrystallizations from hexanes, it yielded 5.8 g of 2-(3,5-di-t-butylphenyl)benz[f]indene (26% yield). 1H-NMR (CDCl3, 300 MHz) delta 7.95-7.77 (m, 4H); 7.52-7.37 (m, 5H); 7.23 (s, 1H); 3.99 (s, 2H); 1.43 (s, 18H).

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, 1-Bromo-3,5-di-tert-butylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BP Corporation North America Inc.; EP1157047; (2003); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 38573-88-5, name is 1-Bromo-2,3-difluorobenzene, belongs to bromides-buliding-blocks compound, 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 38573-88-5, Computed Properties of C6H3BrF2

EXAMPLE 93 (R,S)-3-[4-(2,3-difluorophenyl)piperazin-1-yl]-2-[(R,S)-(2-methoxyphenyl)(1-naphthyl)methyl]-2-methyl-3-oxopropanenitrile (RR,SS)-3-(2-methoxyphenyl)-2-methyl-3-(1-naphthyl)-2-(piperazin-1-ylcarbonyl)propanenitrile (471 mg, 1.14 mmol), 2,3-difluorobromobenzene (200 mg, 1.04 mmol), sodium tert-butoxide (139 mg, 1.45 mmol), tris(dibenzylideneacetone)dipalladium (0) (28 mg, 0.031 mmol), racemic BINAP (39 mg, 0.062 mmol), and toluene (3 mL) were combined in a Carius tube, vacuum degassed, placed under an argon atmosphere, sealed and heated to 80¡ã C. overnight. The reaction was cooled, taken up in diethyl ether, filtered, washed with water, saturated aqueous sodium bicarbonate, brine, dried over MgSO4, filtered, evaporated, and purified on slica gel (10percent hexanes/CH2Cl2) to yield 280 mg of the title compound as an off-white crystal solid. mp 198-200¡ã C.; 1H NMR 500 MHz (DMSO-D6): delta 7.98 (d, 1H, J=7.33 Hz), 7.86 (m, 2H), 7.79 (d, 1H, J=8.25 Hz), 7.54 (t, 1H, J=7.64 Hz), 7.42 (m, 2H), 7.23 (t, 1H, J=7.64 Hz), 7.12 (m, 2H), 7.08 (m, 1H), 7.00 (q, 1H, J=9.01 Hz), 6.79 (m, 2H), 6.01 (s, 1H), 4.01 (s, 3H), 3.73 (bs, 4H), 2.96 (bs, 4H), 1.64 (s, 3H) MS (ESI) m/z 526 ([M+H]+); Anal. calcd for C32H29F2N3O2.0.20H2O: C, 72.63; H, 5.60; N, 7.94. Found: C, 72.65; H, 5.58; N, 7.79.

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; Wyeth; US2005/256132; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 101417-40-7, name is 4-(Bromomethyl)benzo[d][1,3]dioxole, belongs to bromides-buliding-blocks compound, 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 101417-40-7, Quality Control of 4-(Bromomethyl)benzo[d][1,3]dioxole

7.5 g (0.033 mol) of 2,3-dimethoxymethylene benzyl bromide,4.5 g (0.036 mol) of m-hydroxybenzaldehyde and 13.5 g (0.099 mol) of potassium carbonate were dissolved in 80 ml of DMF.The reaction was stirred overnight at 40C. After the reaction was stopped, it was filtered after the temperature was lowered to room temperature.An equal volume of water and ethyl acetate were added to the filtrate and the layers were separated. The aqueous phase was extracted twice with ethyl acetate.The organic phases were combined and washed in the order of saturated sodium bicarbonate solution-water-saturated brine.Anhydrous sodium sulfate was dried for 8 h. The desiccant was filtered off, the solvent was evaporated under reduced pressure, and the residue was separated by silica gel column chromatography.Elution with petroleum ether:ethyl acetate (10:1) to collect the desired components,Evaporation under reduced pressure gave a white solid VId 6.3 g, yield 74.8%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(Bromomethyl)benzo[d][1,3]dioxole, and friends who are interested can also refer to it.

Reference:
Patent; The Chinese People’s Liberation Army Military Academy Of Medical Sciences Poison Pharmaceutical Institute; Zhong Bohua; Zhang Ping; He Xinhua; Shi Weiguo; Fan Shiyong; Yao Yishan; Jia Hongxin; (20 pag.)CN103804341; (2018); B;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 2635-13-4,Some common heterocyclic compound, 2635-13-4, name is 5-Bromobenzo[d][1,3]dioxole, molecular formula is C7H5BrO2, 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.

To a screw cap vial were added Pd(PPh3)2Cl2 (58.3 mg, 81.4 mumol), CuI (31.6 mg, 163 mumol),anhydrous DMF (0.33 mL), 4-bromo-1,2-(methylenedioxy)benzene (10d) (200 muL, 1.63 mmol)and Et3N (2.28 mL, 16.4 mmol) at rt. The solution was bubbled with argon gas for 5 min toremove the dissolved gases. Then, trimethylsilylethyne (350 muL, 2.44 mmol) was added, andthe reaction mixture was stirred at 90 C for 24 h. Upon completion of the reaction, the reaction mixture was concentrated by rotary evaporation. Purification by column chromatography(hexanes) yielded 11d (153 mg, 43%) as a brown liquid.

The synthetic route of 2635-13-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jeong, Yunkyung; Lee, Jooyeon; Ryu, Jae-Sang; Bioorganic and Medicinal Chemistry; vol. 24; 9; (2016); p. 2114 – 2124;,
Bromide – Wikipedia,
bromide – Wiktionary