Category: bromides-buliding-blocks

Synthetic Route of 64248-56-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 64248-56-2 name is 2-Bromo-1,3-difluorobenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A mixture of 2, 6-difluorobromobenzene (125.5 g, 650 mmol) in 98% sulphuric acid (250 ml) was cooled in an ice-water bath and then treated with a 1: 1 mixture of 98% sulphuric acid and fuming nitric acid (100 ml) added at such a rate that the internal temperature never exceeded 35C. Once addition was complete the reaction was stirred at ambient temperature for 3 h then poured onto ice. This mixture was diluted with water (final volume 5 1), the resulting solid collected by filtration, washed with water, then dried under vacuum over phosphorus pentoxide, to afford 2-bromo-1, 3-difluoro-4-nitrobenzene as a cream-coloured solid (145 g, 94%) : 1H NMR (360 MHz, CDCl3) 8 7.10-7. 15 (1H, m), 8.09-8. 16 (1H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-1,3-difluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2003/93272; (2003); A1;,
Bromide – Wikipedia,
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Reference of 21524-34-5, A common heterocyclic compound, 21524-34-5, name is 2-Bromo-1,3,5-triisopropylbenzene, molecular formula is C15H23Br, 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.

A mixture of 2-bromo-1,3,5-triisopropylbenzene (60.1 mg, 212 mumol), Bu3SnH (68.3 muL, 254 mumol), and V-65 (10.5 mg, 42.3 mumol) in THF-d8 (6 mL) was stirred at reflux for 3 h. The mixture was concentrated in vacuo, and the residue was purified by column chromatography on silica gel (hexane) to give 2-deutero-1,3,5-triisopropylbenzene (42.9 mg, 98%). 1H NMR (270 MHz): 1.17 and 1.20 (each as s, 18H, CH3), 2.77-2.88 (m, 3H, CH), 6.89 (s, 2.83H, 2-H, 4-H, 6-H).

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:
Article; Mutsumi, Tomonobu; Iwata, Hiroki; Maruhashi, Kazuo; Monguchi, Yasunari; Sajiki, Hironao; Tetrahedron; vol. 67; 6; (2011); p. 1158 – 1165;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 21120-91-2, name is 7-Bromobicyclo[4.2.0]octa-1,3,5-triene, 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 21120-91-2, SDS of cas: 21120-91-2

To a solution of Formula 5 chemical (3.69g,5mmol) in 50mL dry DMF was added NaH(432mg,18mmol), the mixture was stirred at room temperature for 1h. And 7-bromobicyclo[4.2.0]octa-1,3,5-triene(Br-BCB)(2.75g,15mmol) was added to above solution via syringe. The mixture was heated to 60C and stirred overnight. After quenched with water, the mixture was poured into water to remove DMF. The residue was filtrated and the resulting solid was dissolved with dichloromethane, which was then washed with water. The solvent was removed under vacuum and the residue was extracted with dichloromethane. The product was then obtained by column chromatography on silica gel (65%yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-Bromobicyclo[4.2.0]octa-1,3,5-triene, and friends who are interested can also refer to it.

Reference:
Patent; ROHM AND HAAS ELECTRONIC MATERIALS LLC; DOW GLOBAL TECHNOLOGIES LLC; SPENCER, LIAM; LIU, CHUN; ZHU, MINRONG; MCDOUGAL, NOLAN T; FENG, SHAOGUANG; TREFONAS, PETER; DEVORE, DAVID D; TANG, ZHENGMING; FENG, JICHANG; SOKOLOV, ANATOLIY; (41 pag.)TW2016/25529; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 89359-54-6,Some common heterocyclic compound, 89359-54-6, name is 9-Bromo-1-nonene, molecular formula is C9H17Br, 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.

General procedure: 4.3.1. ((oct-7-en-1-yloxy)methyl)cyclohexane (H1)To a stirred solution of cyclohexylmethanol (6) (492 muL, 4.0 mmol,2 eq) in DMF (7 mL) under argon was added NaH (60% suspension inmineral oil; 160 mg, 4.0 mmol, 2 eq) at 0 C. The suspension was stirredat 0 C for 30 min, then 8-bromodec-1-octene (7) (336 muL, 2.0 mmol,1 eq) was added dropwise to the mixture. The mixture was allowed towarm to room temperature and stirred for 1 h. After the reaction wasquenched with saturated NH4Cl, the whole was extracted with Et2O.The extract was washed with H2O and brine, then dried over MgSO4.The filtrate was concentrated under reduced pressure to give an oilyresidue, which was purified using silica gel chromatography (petroleum ether_EtOAc=40:1) to afford H1 (341 mg, 76% yield) as a colorless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 9-Bromo-1-nonene, its application will become more common.

Reference:
Article; Yang, Haoran; Li, Ying; Chai, Huining; Yakura, Takayuki; Liu, Bo; Yao, Qingqiang; Bioorganic Chemistry; vol. 98; (2020);,
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. 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, A new synthetic method of this compound is introduced below., name: 1-Bromo-2,4,5-trifluorobenzene

Example 7: Preparation of (R)-benzyl 4-oxo-4-(3-(trifluoromethyl)-5,6-dihvdro- ri ,2,41triazolor4,3-aipyrazin-7(8H)-yl)-1 -(2,4,5-trifluorophenyl)butan-2- ylcarbamateA solution of 1 -bromo-2,4,5-trifluorobenzene (638 mg, 3.02 mmol) in THF (5 ml_) was slowly added to a suspension of magnesium turnings (73 mg, 3.02 mmol) in THF (5 ml_). The mixture was allowed to stir for 1 hour at 50 0C. To a solution of (S)-benzyl 1 -iodo-4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro- [1 ,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)butan-2-ylcarbamate (406 mg, 0.76 mmol) in THF (5ml_) at -20 0C, cuprous bromide methylsulfide complex (311 mg, 1.51 mmol) was added. The organomagnesium bromide solution was added dropwise and the mixture was allowed to warm up to room temperature. Once de reaction was completed, NH4CI saturated solution (20 ml_) and AcOEt (20 ml_) were added sequentially. The organic layer was dried with anhydrous Na2SO4, filtered and concentrated. Digestion in toluene:heptane (5:1 ) leads to the precipitation of (R)-benzyl 4-oxo-4-(3- (trifluoromethyl)-5,6-dihydro-[1 ,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-1 -(2,4,5- trifluorophenyl)butan-2-ylcarbamate (221 mg, 54% yield).

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; ESTEVE QUIMICA, S.A.; BARTRA SANMARTI, Marti; RUSTULLET OLIVER, Albert; FERNANDEZ HERNANDEZ, Sara; MONSALVATJE LLAGOSTERA, Montserrat; WO2010/97420; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 876-53-9,Some common heterocyclic compound, 876-53-9, name is 1,3-Dibromoadamantane, molecular formula is C10H14Br2, 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.

Compound 1,3-dibromo-adamantane (3 g, 10 mmol) was dissolved in 30 mL of toluene, and then 250 mg ofAIBN (1.5 mmol), 7 g of tri-n-butyl tin (24 mmol), 3 g of ethyl acrylate (30 mmol) were added in order. The reaction wasrefluxed with at 110 C under nitrogen for 3 hours. The reaction solution was cooled to room temperature and was pouredinto 30 mL of 0.2M aqueous ammonia. After being stirred fully, the organic layer was separated. The aqueous layerswere extracted with ethyl acetate (20 mL34). The organic layers were combined and washed with 30 mL of water and30 mL of saturated sodium chloride solution. The resulting materials were dried with anhydrous sodium sulfate, andsolvent was evaporated under the reduced pressure to give a crude product as a colorless oil, which was separated bysilica column chromatography (petroleum ether : ethyl acetate = 10:1) to give compound NM-011a as a colorless oil (2g, 46.6%). ESI-MS: mlz 337.4 ([M+H]+). 1H-NMR (DMSO-d6, ppm): 1.11 (s, 2 H), 1.15-1.19 (m, 6 H), 1.28-1.39 (m, 12H), 1.53 (s, 2 H), 1.97 (s, 2 H), 2.19-2.24 (m, 2 H), 4.03 (q, 4 H, J=7.1 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,3-Dibromoadamantane, its application will become more common.

Reference:
Patent; Guangzhou Magpie Pharmaceuticals Co., Ltd.; WANG, Yuqiang; LIU, Zheng; YU, Pei; SUN, Yewei; ZHANG, Zaijun; ZHANG, Gaoxiao; SHAN, Luchen; YI, Peng; LARRICK, James; (27 pag.)EP3150574; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 65185-58-2,Some common heterocyclic compound, 65185-58-2, name is 2-Bromophenethylamine, 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.

Step A – Preparation of Int Int 59-1 To a stirred solution of 2-bromophenethylamine (20 g, 0.1 mol) in dichloromethane (200 mL ) was added 2,6-lutidine (1 1.8 g, 0.1 1 mol) and 2,2,2-trifluoroacetic anhydride (23.1 g, 0.1 1 mol) at room temperature. The solution was stirred at room temperature for 3 hrs. The solution was washed with IN hydrochloric acid. The organic layer were washed with brine, dried over anhydrous sodium sulfate then filtered. The filtrate was concentrated in vacuum to give the crude product Int 59-1 which was used directly without further purification. MS-ESI (m/z): 295 (M+H) +.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromophenethylamine, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; COBURN, Craig, A.; MALETIC, Milana, M.; LUO, Yunfu; QI, Zhiqi; LI, Chun Sing; YU, Tingting; WO2015/73308; (2015); A1;,
Bromide – Wikipedia,
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Reference of 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.

Acetic anhydride (2.27 eqiv) was added to a cooled 0 C solution of bromomethylaniline (1.00 eqiv) in chloroform (1.5 mL/mol) while maintaining the temperature below 40 C. The reaction mixture was allowed to warm to room temperature and was maintained for 1 h. Potassium acetate (0.29 eq) and isoamyl nitrite (2.15 eqiv) was added and the reaction mixture was heated at reflux for 18 h. The volatiles were removed under reduced pressure. Water (0.65 L/mol) was added to the residue and the mixture was concentrated. Concentrated hydrochloric acid (1 L/mol) was added to the residue and the mixture was heated at 50 C for 2 h. The mixture was allowed to cool to room temperature and the pH was adjusted to 10 by the slow addition of a 50% aqueous sodium hydroxide solution. The mixture was diluted with water (0.65 L/mol) and was extracted with ethyl acetate (2 x 1.2 L/mol). The combined extracts were washed with brine (1 L/mol) and dried over anhydrous sodium sulfate. The organic solution was filtered through a plug of silica gel (ethyl acetate wash), concentrated, and the residue was triturated with heptane (1 L/mol). The solids were collected by filtration, rinsed with heptane, and dried in a vacuum oven.

The synthetic route of 55289-36-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Memory Pharmaceuticals Corporation; WO2004/29050; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 1073-39-8, 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.

To a mixture of 3-bromobicyclo[4.2.0]octa-1,3,5-triene (1 17 mg, 0.64 mmol) in THF (2 ml) was added dropwise n-BuLi (2.5 M in n-hexane) (0.25 ml, 0.64 mmol) at -78 C under N2. The reaction mixture was stirred at -78C for 30 min. 4-(benzyloxy)-2-methyl-3-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6- (benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzaldehyde ((240 mg, 0.32 mmol) in THF (1 ml) was added dropwise at -78C. The reaction mixture was stirred at -78C for 1 h. Saturated NH4CI (aq) was added and the mixture was extracted with EA thrice. The combined extracts were washed with water, saturated brine and dried over anhydrous Na2S04, then concentrated and purified by chromatography on silica gel (1 :3 EA/PE) to (4-(benzyloxy)-2- methyl-3-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)- tetrahydro-2H-pyran-2-yl)phenyl)(1,2-dihydrocyclo-butabenzen-4-yl)methanol as a yellow oil. MS (ES) m/z: 875.5 [M+Na]+.

The synthetic route of 3-Bromobicyclo[4.2.0]octa-1,3,5-triene 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

Electric Literature of 937046-98-5, 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. 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 4: 7-(4-{[tert-Butyl(dimethyl)silyl]oxy}cyclohex-1-en-1-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine A mixture of tert-butyl(dimethyl) {[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl]oxy}silane (450 mg, 1.33 mmol), 7-bromopyrrolo[2,1-f][1,2,4]triazin-4-amine (283 mg, 1.33 mmol), sodium carbonate (470 mg, 4.4 mmol), and [1,1′-bis(di-cyclohexylphosphino)ferrocene]dichloropalladium (II) (101 mg, 0.133 mmol) in tert-butyl alcohol (4.0 mL) and water (1.5 mL) was degassed with nitrogen, then stirred and heated at 110 C. for 2 h, then 95 C. overnight. The mixture was diluted with ethyl acetate, washed with saturated NaHCO3, water, dried over Na2SO4, filtered and concentrated. The product was purified by Biotage silica gel chromatography (0 to 50% EtOAc in hexanes) to give the desired product as off-white powders (242.3 mg, 53%). LCMS calcd for C18H29N4OSi (M+H)+: m/z=345.2. Found: 345.2.

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, 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Incyte Corporation; Li, Yun-Long; Wang, Xiaozhao; Barbosa, Joseph; Burns, David M.; Feng, Hao; Glenn, Joseph; He, Chunhong; Huang, Taisheng; Mei, Song; Zhuo, Jincong; (169 pag.)US2017/275290; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary