Category: bromides-buliding-blocks

Synthetic Route of 3814-30-0,Some common heterocyclic compound, 3814-30-0, name is (Bromomethyl)cyclopentane, molecular formula is C6H11Br, 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 solution of 3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one (400 mg, 1.82 mmol) in anhydrous DMF (5 mL) was added K2CO3 (503 mg, 3.64 mmol) and (bromomethyl)cyclopentane (445 mg, 2.73 mmol). The reaction mixture was stirred at 60C for 16 hours. The mixture was filtered and the filtrate was purified by preparative LC-MS to afford 7-(cyclopentylmethyl)-3-(tetrahydro-2/-/-pyran-4-yl)imidazo[1 ,5- a]pyrazin-8(7H)-one 290 mg (53%). NMR (DMSO-de, 400 Mhz): delta 7.62 (s, 1 H), 7.49 (d, J = 6.0 Hz, 1 H), 6.90 (d, J = 6.0 Hz, 1 H), 3.91 -3.88 (m, 2H), 3.69 (d, J = 7.6Hz, 2H), 3.48-3.43 (m, 2H), 3.42-3.31 (m, 1 H), 2.27- 2.24 (m, 1 H), 1.78-1.73 (m, 4H), 1.58-1.44 (m, 6H) , 1.21 -1.20 (m, 2H). LC-MS: (m/z) 302.2 (MH+) tR (minutes, method 3) = 2.29 minutes .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Bromomethyl)cyclopentane, its application will become more common.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (157 pag.)WO2018/78038; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 117635-21-9, The chemical industry reduces the impact on the environment during synthesis 117635-21-9, name is 1,4-Dibromo-2,5-dihexylbenzene, I believe this compound will play a more active role in future production and life.

[N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-[1,1′-biphenyl]-4-amine](15) (1.2g, 3.3mmol)And 1,4-dibromo-2,5-dihexylbenzene] (16) (0.6 g, 1.5 mmol)To this reaction flask is added toluene / EtOH / 2N K2CO3 (aq) (2v: 1v: 1v) solvent.Degassing using a vacuum pump. Pd (PPh3) 4 (347 mg, 0.3 mmol) was added to the reaction flask and stirred at 90 for one day. Ethanol was removed using a vacuum evaporator and organic matter was extracted with dichloromethane (DCM). The organic layer was dried over MgSO4, filtered and purified by column to obtain 730 mg (yield 66%) of Intermediate 17

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, 1,4-Dibromo-2,5-dihexylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LG Chem, Ltd.; Kang Seong-gyeong; Bae Jae-sun; Lee Jae-cheol; Yoon Seok-hui; Lee Dong-gu; Kim Yong-uk; Lee Ho-gyu; (54 pag.)KR2018/92270; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 51437-00-4, 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 51437-00-4 as follows.

To a solution of diisopropylamine (1.77g, 17.5 mmol, 1.1 eq) in THF (20 mL) was added n-BuLi (7.3 mL, 2.4 M in THF, 17.5 mmol, 1.1 eq) at -78C under N2. The mixture was stirred at -78C for lh, then a solution of 4-bromo-l-fluoro-2 -methyl-benzene (3 g, 15.8 mmol, 1.0 eq ) in THF (20 mL) was added dropwise. The reaction was stirred a further 2h at -78C then C02 gas was bubbled into the mixture for 30 min. The reaction was quenched by addition of water and acidified to pH 3 by addition of 1M HCl. The aqueous layer was extracted with EtOAc and the combined organic extracts were washed with brine, dried (Na2S04), filtered and evaporated in vacuo. The residue obtained was purified by chromatography to give the title compound as a white solid (697 mg, 21 %).LC-MS : m/z 230.9, 232.9 [M-H]” HNMR (400 MHz, DMSO-d6) ? 7.94 – 7.59 (m, 2H), 2.26 (s, 3H)

According to the analysis of related databases, 51437-00-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FOVEA PHARMACEUTICALS; FEUTRILL, John; LERICHE, Caroline; MIDDLEMISS, David; WO2013/37705; (2013); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 10269-01-9, The chemical industry reduces the impact on the environment during synthesis 10269-01-9, name is (3-Bromophenyl)methanamine, I believe this compound will play a more active role in future production and life.

(4?-(Trifluoromethyl)biphenyl-3-yl)methanamine. A 1 00-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with (3- bromophenyl)methanamine (570 mg, 3.0 mmol), 4-(trifluoromethyl)phenylboronic acid (558 mg, 3.0 mmol), Pd(PPh3)4 (173 mg, 0.15 mmol), K3P04 (1.91 g, 9.0 mmol), DME (30 mL) and H20 (6 mL). The system was subject to 3 cycles of vacuum/argon flush and heated at reflux for overnight. The mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 1:20 MeOH/CH2C12 to afford the title compound (640 mg, 85%) as brown solid. MS-ESI: [M+H] 252.1.

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, (3-Bromophenyl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BROTHERTON-PLEISS, Christine E.; CHEN, Huifen; CHEN, Shaoqing; CHEN, Zhi; ERICKSON, Shawn David; ESTRADA, Anthony; KIM, Kyungjin; LI, Hongju; LOVEY, Allen John; LYSSIKATOS, Joseph P.; QIAN, Yimin; SO, Sung-Sau; WOVKULICH, Peter Michael; YI, Lin; WO2014/49047; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

73918-56-6, name is 2-(4-Bromophenyl)ethanamine, 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. Patent; INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION; ASSEMBLY BIOSCIENCES, INC.; TURNER, William W.; ARNOLD, Lee Daniel; MAAG, Hans; ZLOTNICK, Adam; WO2015/138895; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 766-46-1, 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. 766-46-1, name is 2′-Bromophenylacetylene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

under high purity nitrogen atmosphere, into 10ml of Schlek reaction tube was 0.02mmol benzoquinolin triphenylphosphine ring iridium hydrogen adduct material (4), 1mmol2- bromophenyl acetylene, 2mmol benzyl alcohol, and 1.0 mmol of potassium carbonate in 3ml of toluene, the reaction tube was replaced with nitrogen 3 times, then in an oil bath with magnetic stirring and heated to 110 deg.] C, the reaction was refluxed for 20 hours. Oil bath was removed, the water bath to room temperature; 3ml adding water to the reaction liquid, extracted three times with 5ml of dichloromethane, and the combined organic phases were dried over anhydrous MgSO4 for 30 minutes and filtered; the filtrate was concentrated on a rotary evaporator, the remaining oil residue ether as eluent, separated by thin layer chromatography on silica gel to give the pure product 1-phenyl-3 (2-bromophenyl) -1-propanone, yield 88%.

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

Reference:
Patent; Luoyang Normal University; Li, Xiao Dong; Li, gongmei; Xu, Chen; Hao, Xin Qi; Xiao, Zhi Qiang; (10 pag.)CN103242372; (2016); B;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 51437-00-4, name is 4-Bromo-1-fluoro-2-methylbenzene, 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 51437-00-4, Quality Control of 4-Bromo-1-fluoro-2-methylbenzene

Step 1. 5-Bromo-2-fluoro-3-methylbenzaldehyde: To a stirred solution of di- isopropyl amine (4.01 g, 39.88 mmol) in THF (20 mL) was added n-butyl lithium (1.6 M in hexane) (19.9 mL, 31.91 mmol) at -78 C slowly dropwise over the period of 10 min, the reaction mixture was stirred at -78C for 30 min. A solution of 4-bromo-l-fluoro-2- methylbenzene (5.0 g, 26.6 mmol) in THF (30.0 mL) was added at -78C, and the reaction mixture was stirred for lh at the same temperature. DMF (5.0 mL) was added and stirred at – 78C for another 30 min. The reaction was monitored by TLC; then the reaction mixture was quenched with IN HC1 solution (aq) at 0C. The aqueous layer was extracted with diethyl ether, washed with water and saturated brine solution. The combined organic layer was dried over anhydrous Na2S04 and concentrated under reduced pressure to obtain the crude compound purified by flash column chromatography (Si02, 100-200 mesh; eluting with 5% ethyl acetate/ pet ether) to afford the title compound as a white solid (3.6 g, 64 ); mp 48- 50C: ]H NMR (400 MHz, CDC13) delta 8.33 (s, 1H), 8.22 (s, 1H), 7.67 (s, 1H), 7.60 (s, 1H), 6.75 (dd, J = 17.6, 10.8 Hz, 1H), 5.92 (dd, J = 17.6, 10.8 Hz, 1H), 5.52 (d, J = 17.6 Hz, 1H), 2.21 (s, 3H); ESIMS m/z 211.35 ([M-H]”).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-1-fluoro-2-methylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; DOW AGROSCIENCES LLC; LO, William C.; HUNTER, James E.; WATSON, Gerald B.; PATNY, Akshay; IYER, Pravin S.; BORUWA, Joshodeep; WO2014/100163; (2014); A1;,
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.

EXAMPLE 1 This example illustrates the synthesis of several compounds that are used as intermediates for the synthesis of other compounds. 1-(8,9-Oxidononyl)-3,7-dimethylxanthine was synthesised as follows: A mixture of theobromine (17.64 g, 98 mmol) and sodium hydride (2.35 g, 98 mmol) in dimethylsulfoxide (250 ml) was stirred for 15 minutes. 9-Bromo-1-nonene (20.0 g, 98 mmol) was added and stirring continued for 3 days. The reaction mixture was poured into water (300 ml) and extracted with dichloromethane (4*200 ml). The combined organic layers were washed with saturated aqueous sodium chloride solution (2*150 ml), dried over sodium sulfate, and the solvents evaporated under vacuum. The residue was crystallized (dichloromethane-ether) to give 1-(8-nonenyl)-3,7-dimethylxanthine (24.34 g, 99% yield) as white crystals.

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:
Patent; Cell Therapeutics, Inc.; US5641783; (1997); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 67567-26-4, name is 4-Bromo-2,6-difluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H4BrF2N

Compound 121 : 4-(9-Cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9- tetrahydro-5H-pyrimido[4,5-b][l,4]diazepin-2-ylamino)-3-fluoro-5-methoxybenzoic acid; [0581] 5-Bromo-l,3-difluoro-2-nitrobenzene: To a mixture of acetic acid (30 mL), 30% H2O2 (20 mL) and concentrated sulfuric acid (1 mL) was added l-bromo-2,6- difluoroaniline (5 g, 24 mmol) in acetic acid (10 mL) dropwise at 85 0C. The reaction mixture was heated for 1 h. It was then cooled down, diluted to water and extracted with ethyl acetate. The organic layer was dried and concentrated to a red residue, which was purified by flash column (EtOAc in Hexane 2-5%) to give the product as yellow solid (2.7 g, 47%). 1H NMR (400 MHz, CHLOROFORM-J) delta ppm 7.33 (m, 2 H).

According to the analysis of related databases, 67567-26-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2009/42711; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary