Bromides-buliding-blocks

Some common heterocyclic compound, 1422-54-4, name is 2-Bromo-6-fluorotoluene, molecular formula is C7H6BrF, 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. Formula: C7H6BrF

0.867 g (35.67 mmol) of magnesium turnings were dried and suspended in 17 ml of anhydrous THF under argon. A solution of 1 ,2-dibromoethane (0.14 ml, 1.62 mmol) and 2-bromo-6-fluoro-toluene (6.74 g, 35.67 mmol) in 17 ml of anhydrous THF was then added dropwise so as to maintain a gentle reflux. Once the magnesium had been consumed, copper(l) iodide (0.432 g, 2.27 mmol) was then added, followed by a solution of epichlorohydhne (3.00 g, 32.42 mmol) in DMF (8 ml). The mixture was stirred for 3.5 h at room temperature and then quenched with a saturated solution of ammonium chloride (120 ml). The organic layer was separated, and the aqueous phase was extracted twice with EA. The combined organic phases were washed twice with a saturated solution of ammonium chloride, dried over sodium sulfate, filtered and evaporated to dryness. The product was purified by chromatography on silica gel (cyclohexane/EA, from 100:0 to 90:10) to give 6.89 g of 1-chloro-3-(3-fluoro- 2-methyl-phenyl)-propan-2-ol. 3.92 g (16.23 mmol) of this alcohol were dissolved in DCM under argon, and 1 ,1 ,1-thacetoxy-1 ,1 -dihydro-1 ,2-benziodoxol-3(1 H)-one (Dess-Martin periodinane reagent; 7.57 g, 16.23 mmol) was added. The mixture was stirred at room temperature overnight and then diethyl ether (150 ml) was added. The mixture was washed three times with 1 N hydrochloric acid (70 ml) and twice with a saturated solution of sodium chloride, and extracted with ether. The extracts were dried over sodium sulfate, filtered and evaporated to dryness. 2.69 g of the title compound were obtained as a white powder.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1422-54-4, its application will become more common.

Reference:
Patent; SANOFI-AVENTIS; STEINHAGEN, Henning; SCHEIPER, Bodo; MATTER, Hans; MCCORT, Gary; BEGIS, Guillaume; GOBERVILLE, Pascale; THIERS, Berangere; WO2011/12538; (2011); A1;,
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Reference of 1422-53-3,Some common heterocyclic compound, 1422-53-3, name is 2-Bromo-4-fluorotoluene, molecular formula is C7H6BrF, 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.

The compound of formula 3 (5.0 g, 26.5 mmol, 1.0 equiv) and 98% concentrated sulfuric acid (50 ml) were added to a 100 ml three-necked flask.The solution was cooled to 0 C to 5 C and potassium nitrate (3.5 g, 34.6 mmol, 1.3 equiv) was added in portions.And reacted at 25 C for 2 hours under nitrogen protection. After completion of the reaction, the reaction solution was poured into a large amount of ice water,Ethyl acetate extraction. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, Concentrate under reduced pressure. The crude product was purified by silica gel column chromatography (petroleum ether) to give 3.4 g of the compound of formula 4 as a yield of 54.3%.

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-4-fluorotoluene, its application will become more common.

Reference:
Patent; Shanghai Acebright Pharmaceuticals Group Co., Ltd.; Yu, Libing; Guo, Maojun; Yang, QinGang; Liu, Huixin; (23 pag.)CN105646333; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 103-64-0, A common heterocyclic compound, 103-64-0, name is (2-Bromovinyl)benzene, molecular formula is C8H7Br, 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.

At room temperature,To the appropriate amount of the organic solvent DMF was added 100 mmol of the compound of the above formula (I)250 mmol of the compound of formula (II)4 mmol of catalyst (1 mmol of Pd (TFA) 2 with 3 mmol of Cu (acac) 2)35 mmol of 1-ethyl ethyl ether-3-methylimidazolebis (trifluoromethanesulfonyl) imide salt and 250 mmol of triisopropanolamine,Then heated to 70 C,And the reaction was stirred at that temperature for 8 hours; After the reaction,The resulting mixture was filtered while hot,To obtain a filtrate;To the filtrate was added a 10% hydrochloric acid solution with a mass percentage of 10%Adjust the pH to neutral;Then ethyl acetate,Oscillation extraction 2-3 times,Combined organic phase,Dried over anhydrous magnesium sulfate,Then concentrated under reduced pressure,The resulting residue was subjected to 200-300 mesh silica gel column chromatography,The petroleum ether-n-butanol mixture was used as the eluent,Wherein the volume ratio of petroleum ether to n-butanol is 9: 1,Thereby obtaining a compound of the above formula (III)The yield was 97.3%.

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; Qingdao University; Xia Yunqiu; Zhou Yingbin; Wang Yanxin; Zhong Weizhen; Guo Shenbo; (9 pag.)CN104803912; (2017); B;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 698-00-0, The chemical industry reduces the impact on the environment during synthesis 698-00-0, name is 2-Bromo-N,N-dimethylaniline, I believe this compound will play a more active role in future production and life.

Example No. 6: Preparation of Compound No. 6[0294] A solution of 2,8-dimethyl-2,3,4,5-tetrahydro- lH-pyrido[4,3-b]indole (0.2 g, 1 mmol), (2-bromo-phenyl)-dimethyl-amine (600 mg, 3 mmol), K3PO4 (636 mg, 3 mmol), L-Proline (69 mg, 0.6 mmol) and Cul (57 mg, 0.3 mmol) in dry DMF (4 mL) was stirred at 150 C for 16h. The reaction mixture was cooled to RT, diluted with water and extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude material, which was purified by column chromatography using neutral alumina and 10% EtOAc-Hexane followed by reverse phase HPLC purification to yield [2-(2,8- dimethyl-l,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-phenyl]-dimethyl-amine (20 mg). 1H NMR (TFA salt, CD3OD) delta (ppm): 7.50 (m, 1H), 7.38 (m, 2H), 7.18 (m, 2H), 7.0 (m, 2H), 4.75 (d, 1H), 4.40 (m, 1H), 3.80 (m, 1H), 3.58 (m, 1H), 3.15 (s, 3H), 3.0 (m, 1H), 2.70 (m, 1H), 2.56 (s, 6H), 2.42 (s, 3H).

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-dimethylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; PROTTER, Andrew, Asher; CHAKRAVARTY, Sarvajit; WO2012/112962; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 344-03-6, 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. 344-03-6, name is 1,4-Dibromotetrafluorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

(A) Preparation of starting materials Synthesis of dimethylaminomethyl p-bromotetrafluorobenzene 10 g (32.5 mmoles) of 1,4-dibromotetrafluorobenzene are dissolved under argon in 100 ml of ether and 100 ml of tetrahydrofuran. The solution is cooled to -78¡ã C. and 21 ml of a 1.6 molar solution of butyllithium in hexane are added. After 15 minutes, 6.08 g (65 mmoles) of N,N-dimethylmethyleneimmonium chloride are added and the mixture is warmed to room temperature. After 11/2 hours the mixture is poured into water and extracted with ether. The ethereal extract is dried over MgSO4. The solvent is distilled off, affording as residue a white solid which is distilled at 100¡ã C. under a high vacuum. Yield: 7.8 g (84percent) of a colourless product which is solid at room temperature.

The chemical industry reduces the impact on the environment during synthesis 1,4-Dibromotetrafluorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Ciba-Geigy Corporation; US4590287; (1986); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 10016-52-1,Some common heterocyclic compound, 10016-52-1, name is 2,8-Dibromodibenzo[b,d]furan, molecular formula is C12H6Br2O, 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 two-necked flask were added A-1-1 (2.5 g), B-1 (3.6 g) And sodium tert-butoxide (4.4 g) was added thereto. The flask was filled with di-gassed toluene (46 mL) and heated to 100 C. Pd [P (t-Bu) 3] 2 (200 mg), Pd And the mixture was stirred at the same temperature for 17 hours. Diluted with DCM (100 mL) and filtered through SiO2. The filtered solution was depressurized to remove the solvent, and the residue was dissolved in THF in EA and then recrystallized to obtain A-1 (final) (1.5 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,8-Dibromodibenzo[b,d]furan, its application will become more common.

Reference:
Patent; LG Chem, Ltd.; Lee Chung-hwan; Bae Jae-sun; Lee Jae-cheol; Kim Hwa-gyeong; Shin Ji-yeon; (37 pag.)KR2018/92782; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 67567-26-4, name is 4-Bromo-2,6-difluoroaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 67567-26-4

4-Bromo-2,6-difluoroaniline (65A, 0.50Og, 2.4mmol) was combined with sodium methanesul finale (0.98g, 9.6mmol), cuprous triflate benzene complex (0.121g, 0.24mmol), and N,N’-dimethylethylencdiamine (0.027mL, 0.23mmol) in DMF (5mL). The mixture was heated to 150 C and allowed to stir at this temperature for 24 hours, then was concentrated in vacuo and purified using PLC to provide compound 65B as a yellow solid.

The synthetic route of 67567-26-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2009/55331; (2009); A2;,
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bromide – Wiktionary

Synthetic Route of 1647-26-3, A common heterocyclic compound, 1647-26-3, name is 1-Bromo-2-cyclohexylethane, molecular formula is C8H15Br, 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.

Example 2; Synthesis of 3-(2-aminoquinazolin-6-yl)-1-(2-cyclohexylethyl)-4- methylpyridin-2(1 K)-one; To a solution of 3-(2-aminoquinazolin-6-yl)-4-methylpyridin-2(1 H)-one (103mg, 408 mumol, Example 1 , step 3) in DMF in a sealed tube was added sodium tert- butoxide (58.9 mg, 612 mumol). The mixture was stirred at RT for 5min and turned from clear yellow to a suspension of yellow solids. 1-bromo-2-cyclohexylethane (76.7 mul, 490 mumol) was then added and the resulting mixture was heated to 700C over the weekend. Reaction was cooled to RT and was quenched with Sat’d NH4CI and extracted with DCM. Purification by prep plate TLC (10% MeOH/DCM) produced the title compound as an off white solid. M+H= 363.2.

The synthetic route of 1647-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; WO2008/11109; (2008); A2;,
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. 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 327-51-5

1,4-dibromo-2, 5-difluorobenzene (49.3 g, 181.5 mmol), 2-methoxyphenylboronic acid (66.2 g, 435.6 mmol), a 2 M aqueous solution of Na2CO3 (363 mL, 726 mmol), DME (360 mL), toluene (360 mL), and Pd[PPh3]4 (21 g, 18.0 mmol) were loaded into a three-necked flask, and the mixture was refluxed under an Ar atmosphere for 8 hours. After the completion of the reaction, the resultant was cooled to room temperature. The resultant sample was transferred to a separating funnel, and water (500 mL) was charged into the funnel. Then, the mixture was extracted with CH2Cl2. The extract was dried with MgSO4, and was then filtrated and concentrated. The resultant sample was purified by silica gel column chromatography, whereby a white solid was obtained in an amount of 38.5 g in 65% yield. FD-MS C20H16F2O2 : theoretical value 326, observed value 326

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 327-51-5.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; EP2301921; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 630-17-1, name is 1-Bromo-2,2-dimethylpropane, 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 630-17-1, COA of Formula: C5H11Br

Example 2: Synthesis of posphoric acid mono-[2-(2, 2-dimethyl-propane-1-sulfonyl)-ethyl] ester A. 2-(2, 2-Dimethyl-propane-1-sulfonyl)-ethanol; A suspension of 2-mercapto-ethanol (110 mg, 1.41 mmol), 1-bromo-2, 2-dimethyl-propane (210 mg, 1.41 mmol) and K2C03 (195 mg, 1.41 mmol) in DMF (3 mL) was stirred at 60 C for 5 h. The reaction mixture was then cooled to room temperature and treated with a mixture of 2KHS05-KHS04 (1.30 g, 2.11 mmol) in water (0.5 mL). After stirring for 12 h at room temperature, the solvent was removed in vacuo, and the residue partitioned between ethyl acetate and water. The organic layer was dried over Na2S04, filtered, and concentrated in vacuo. The residue was purified by flash chromatography over silica gel (elution with hexane/ethyl acetate 4: 1) to give the title compound as a colorless oil. 1H NMR (300 MHz, DMSO-d6) 6 1.23 (s, 9H), 2.55 (s br. , 1H), 3.05 (s, 2H), 3.18-3. 23 (m, 2H), 4.09-4. 19 (m, 2H).

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; JERINI AG; WO2005/80406; (2005); A2;,
Bromide – Wikipedia,
bromide – Wiktionary