Bromides-buliding-blocks

Some common heterocyclic compound, 2695-48-9, name is 8-Bromo-1-octene, molecular formula is C8H15Br, 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. 2695-48-9

1-(7,8-Dihydroxyoctyl)-3,7-dimethylxanthine was used as an intermediate for the synthesis of inventive compound no. 1514 (example 12). To a suspension of sodium hydride (580 mg, 24.2 mmol) in dimethylsulfoxide (100 ml) was added theobromine (3.96 g, 22.0 mmol). After stirring for 30 min, 8-bromo-1-octene (3.96 g, 22 mmol) was added and the mixture was stirred for 16 hr. The mixture was poured into water (200 ml) and extracted with dichloromethane (3*50 ml). The combined organic layers were washed with saturated aqueous sodium chloride solution (50 ml), dried over sodium sulfate, and the solvent was evaporated under vacuum to give 1-(7-octenyl)-3,7-dimethylxanthine (6.22 g, 97% yield) as an oil which solidified upon standing.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2695-48-9, its application will become more common.

Reference:
Patent; Cell Therapeutics, Inc.; US6020337; (2000); A;,
Bromide – Wikipedia,
bromide – Wiktionary

108-85-0, A common compound: 108-85-0, name is Bromocyclohexane, 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.

Example 9 (E)-2-(3-Chloro-4-methanesulfonyl-phenyl)-2-cyclohexyloxyimino-N-(1-methyl-1H-pyrazol-3-yl)-acetamide Solid potassium carbonate (6.91 g, 50.0 mmol) was added to a solution of N-hydroxyphthalimide (4.08 g, 25.0 mmol) and 18-crown-6 (661 mg, 2.5 mmol) in dimethyl sulfoxide (62 mL), and the mixture was stirred at 25 C. for 5 min. To the mixture cyclohexyl bromide (12.3 mL, 100.0 mmol) was added, and the mixture stirred at 80 C. for 3 h. After ice-cooling, the mixture was poured into cold water and the resulting precipitate was collected by filtration in vacuo, washed with water (25 mL) and hexanes (15 mL) and dried in vacuo to afford 2-cyclohexyloxy-isoindole-1,3-dione (5.67 g, 93%) as a white solid which was used in the next step without further purification.

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, Bromocyclohexane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Berthel, Steven Joseph; Kester, Robert Francis; Murphy, Douglas Eric; Prins, Thomas Jay; Ruebsam, Frank; Tran, Chinh Viet; Vourloumis, Dionisios; US2008/146625; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 67567-26-4 name is 4-Bromo-2,6-difluoroaniline, 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. 67567-26-4

The compound of formula XIV-1 (31.05 g, 0.15 mol), the compound of formula XIII-1 (30.3 g, 0.30 mmol)Phosphorus oxychloride(20.9 mL, 0.225 mol) were added sequentially to anhydrous toluene. Triethylamine (31.3 mL, 0.225 mol) was added in an ice bathConstant pressure funnel slowly added dropwise to the reaction flask,Maintain the internal temperature is less than 60 .The reaction flask was transferred to an oil bath and heated to reflux.After 2 hours, the reaction flask was cooled to room temperature, slowly poured into 300 g of ice water mixture, 300 ml of ethyl acetate was added, sufficientAfter the mixture was separated, the aqueous layer was extracted with 200 ml of ethyl acetate again. The combined organic layers were washed with saturated brine and dried over anhydrous sulfuric acidSodium dried, concentrated under reduced pressure to give a pale yellow solid, beaten with 100 ml of petroleum ether for 10 minutes, filtered under reduced pressure to give a compound of formulaCompound XV-1 (28.0 g) as an off white solid (yield 92.3%)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2,6-difluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Zhang Yinsheng; Liu Yingshuai; Qin Hui; Li Yuan; Zhao Kaidi; Miao Lei; Hu Jie; Liu Haiyan; Wang Xiaojin; (33 pag.)CN107266421; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

A common heterocyclic compound, 22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, molecular formula is C14H21Br, 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. 22385-77-9.

Compound 9 (12.2 g, 24.5 mmol) was dissolved in THF (100 mL) and cooled to -78 ¡ãC. To thissolution was added at -78 ¡ãC a freshly prepared solution of LDA from diisopropylamine (5.15 mL, 36.7mmol) and n-BuLi (22.2 mL, 1.65 M, 36.7mmol) in THF (50 mL). After stirring at -78 ¡ãC for 30 min, the resulting solution was added to asuspension of ZnCl2 (12.1 g, 89.1mmol) in THF (100 mL) at -78 ¡ãC. The reaction mixture was stirred at -78 ¡ãC for 1 h and warmed to room temperature, where stirring was continued for 1 h. The resulting solution was added to a solution of 1-bromo-3,5-di-t-butylbenzene (6.60 g, 24.5mmol) and [Pd(PPh3)4] (1.42 g, 1.22 mmol) in THF (50 mL). The resulting solution was heated at 60 ¡ãC for 10 h, before the reaction was quenched by addition of saturated aqueous sodium hydrogen carbonate. The reaction mixture was extracted with Et2O and the combined organic phases were washed with water and dried over MgSO4. After filtration and evaporation of all volatiles under reduced pressure, the obtained residue was purified by column chromatography on silica gel (hexane/ethyl acetate 1:1) to give10 (13.5 g, 19.7mmol, 80percent).

The synthetic route of 1-Bromo-3,5-di-tert-butylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sakagami, Michiyasu; Sasamori, Takahiro; Sakai, Heisuke; Furukawa, Yukio; Tokitoh, Norihiro; Bulletin of the Chemical Society of Japan; vol. 86; 10; (2013); p. 1132 – 1143;,
Bromide – Wikipedia,
bromide – Wiktionary

2606-51-1, Adding a certain compound to certain chemical reactions, such as: 2606-51-1, name is 5-(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 2606-51-1.

To a suspension of 6-methyl-3-(tetrahydro-2H-pyran-4-yl )imidazo[1 ,5-a]pyrazin-8(7H)-one(100 mg, 429 pmol) in dry DMF (2 mL) was added 052003 (279 mg, 858 pmol) and 5-(bromomethyl)benzo[d][1 ,3]dioxole (138 mg, 643 pmol). The mixture was bubbled with N2 for 2 mm and heated at 6000 for 16 hours. The mixture was concentrated. DCM (30 mL) was added to the residue. It was filtered and the filter cake was washed with DCM (20 mL). The filtrate was concentrated and purified by flash chromatography on silica gel (1O%-100%ethyl acetate in petroleum ether) to give 7-(benzo[d][1 ,3]dioxol-5-ylmethyl)-6-methyl-3- (tetrahydro-2H-pyran-4-yl)imidazo[1 ,5-a]pyrazin-8(7H)-one (81.74 mg, 52% yield).1H NMR (ODd3 400 MHz): 7.92 (s, 1 H), 6.76 – 6.69 (m, 4H), 5.95 – 5.93 (m, 2H), 5.13 (s,2H), 4.14 – 4.11 (m, 2H), 3.61 – 3.55 (m, 2H), 3.10 – 3.05 (m, 1 H), 2.21 (s, 3H), 2.20 – 2.10(m, 2H), 1.90 – 1.86 (m, 2H).LC-MS: tR = 2.245 mm (method 3), mlz = 368.2 [M + H].

According to the analysis of related databases, 2606-51-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (159 pag.)WO2016/174188; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 58971-11-2 name is 3-Bromophenethylamine, 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. 58971-11-2

A solution of 2- (3-bromophenyl) ethylamine (2 g, 10 mmol)Was dissolved in dichloromethane (30 mL)To this was added triethylamine (3 mL, 20.99 mmol) andAcetic anhydride (2 mL, 20.99 mmol).The reaction mixture was stirred at room temperature overnight, followed by water (50 mLx3), brine (50 mL x 3), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product (2.42 g, 100%).

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

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Wang Ruyong; Wang Liang; (112 pag.)CN104016979; (2017); B;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding some certain compound to certain chemical reactions, such as: 1575-37-7, name is 4-Bromobenzene-1,2-diamine, 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 1575-37-7. 1575-37-7

A 250 mL four-necked flask equipped with a mechanical stirrer, thermometer, reflux condenser, nitrogen inlet and bubble counterEach o-diaminobenzene (0.031 mol) (Formula 1a) was added dropwise to glacial acetic acid (50 mL) under a nitrogen atmosphere.The resulting slurry was cooled to 4 [deg.] C in an ice-bath. Sodium nitrite in water (6 mL) (2.24 g,0.032 mol) in THF Was added dropwise over 40 minutes while maintaining the temperature of the reaction mixture below & lt; RTI ID = 0.0 & gt; 10 C. & lt; / RTI & gt; GeneratedThe slurry was allowed to warm to room temperature and analyzed using a KI / amylose test paper until analysis for free HNO2 was negative and starting material was not visible in thin layer chromatography (16 h)Under stirring. The resulting slurry was filtered; the solid residue washed with water (100 mL) and the resulting solid was further purified by recrystallization from ethanol (20 mL). The product was dried for 24 h at 50 C. and 5 mbar and obtained as off-white solid. Yield: 67%.

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 4-Bromobenzene-1,2-diamine.

Reference:
Patent; BASF SE; Reihard, Robert; Kalor, Martin; Router, Michael; Li, Yuchuo; Cliff, Andreas; (31 pag.)KR2016/30566; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

1003-98-1,Some common heterocyclic compound, 1003-98-1, name is 2-Bromo-4-fluoroaniline, molecular formula is C6H5BrFN, 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 15 (67.5 g, 0.355 mol) was added to the 300 mL 15 % aq. HCl. A resulting suspension was stirred for 1 h at 80 oC, then cooled to -5 C and NaNO2 (26.0 g, 0.365 mol) in H2O (50 mL) was slowly added. The mixture was stirred for 1.5 h at -5 C and then the excess of HNO2 was neutralized with urea. The solution of KI (57.2 g, 0.0355 mol) in 50 mL H2O was added dropwise at 0 oC (caution, the fast evolution of N2 was observed). The mixture was warmed to room temperature and stirred for 40 h. After this time CHCl3 was added, water phase was extracted with CHCl3 (3 ¡Á 100 mL), joined organic phases were washed with saturated solution of NaHCO3 (200 mL), 5% solution of Na2S2O3 (200mL) and5% solution of Na2S2O5 (200mL). Organic phase was dried over MgSO4 and concentrated under reduced pressure. The obtained crude product was distilled under reduced pressure (b.p. 90-91 oC, 2 Tr) affording 17 as viscous oil (69.1 g, 64%). 1H NMR (400 MHz, CDCl3): delta 7.79 (ddd, J = 9.0, 5.8, 0.9 Hz, 1H), 7.38 (ddd, J = 8.3, 2.9, 0.8 Hz, 1H), 6.78 (ddd, J = 9.0, 7.9, 2.9 Hz, 1H) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1003-98-1, its application will become more common.

Reference:
Article; Durka, Krzysztof; Laudy, Agnieszka E.; Charzewski, ?ukasz; Urban, Mateusz; St?pie?, Karolina; Tyski, Stefan; Krzy?ko, Krystiana A.; Luli?ski, Sergiusz; European Journal of Medicinal Chemistry; vol. 171; (2019); p. 11 – 24;,
Bromide – Wikipedia,
bromide – Wiktionary

201138-91-2, The chemical industry reduces the impact on the environment during synthesis 201138-91-2, name is 4,6-Dibromodibenzo[b,d]furan, I believe this compound will play a more active role in future production and life.

Add 32.4g (100mmol) 4,6-dibromodibenzothiophene and 112.8g (300mmol) 2-formylbenzeneboronic acid to a freshly dried 3000mL two-necked bottle, add 62.1g (450mmol) under nitrogen protection Anhydrous potassium carbonate, 6.9 g (6 mmol) of tetratriphenylphosphine palladium, and 225 mL of water and 1500 mL of 1,4-dioxane. After the reaction, the temperature was lowered to room temperature, and the solvent of the reaction system was distilled off under reduced pressure. The crude product was dissolved in 500 mL of dichloromethane and washed with a large amount of water. The organic phase was dried over anhydrous sodium sulfate and concentrated. Dichloromethane: petroleum ether = 1: 1 was used as the eluent for column chromatography to obtain 30 g of off-white solid with a yield of 80%.

The chemical industry reduces the impact on the environment during synthesis 4,6-Dibromodibenzo[b,d]furan. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Beijing Dingcai Technology Co., Ltd.; Wei Jinbei; Li Guomeng; Gao Wenzheng; Sun Lei; (35 pag.)CN110878054; (2020); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding some certain compound to certain chemical reactions, such as: 3972-65-4, name is 1-Bromo-4-(tert-butyl)benzene, 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 3972-65-4. 3972-65-4

General procedure: An oven-dried 10 mL reaction vial equipped with a stir bar was charged with Pd(OAc)2 (1.12mg, 0.005 mmol) and 3a (2.7 mg, 0.0075 mmol) under a nitrogen atmosphere, and 0.5 mL of dry toluene was added to the mixture. After stirring for 5 min at room temperature, NaN(SiMe3)2 (55 mg, 0.3 mmol, 3 equiv) was added to the reaction vial. After stirring for another 15 min at room temperature, 4-benzylpyridine (20.3 mg, 0.12 mmol, 1.2 equiv) was added to the reaction mixture followed by 1-bromo-4-tert-butylbenzene (21.3 mg, 0.1 mmol, 1 equiv). The reaction mixture was stirred for 16 h at 60 C, quenched with two drops of H2O, diluted with 3 mL of ethyl acetate, and filtered over a pad of MgSO4 and silica. The pad was rinsed with additional ethyl acetate, and the solution was concentrated in vacuo. The crude material was loaded onto a silica gel column and purified by flash chromatography.

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 1-Bromo-4-(tert-butyl)benzene.

Reference:
Article; Zhou, Bi-Hui; Wu, Chen; Chen, Xing-Xiu; Huang, Hong-Xia; Li, Lin-Lin; Fan, Li-Mei; Li, Jie; Tetrahedron Letters; vol. 58; 44; (2017); p. 4157 – 4161;,
Bromide – Wikipedia,
bromide – Wiktionary