Author: Jessica.F

Electric Literature of 138526-69-9, A common heterocyclic compound, 138526-69-9, name is 1-Bromo-3,4,5-trifluorobenzene, molecular formula is C6H2BrF3, 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.

General procedure: PN (0.004 mol) was dissolved in anhydrous tetrahydrofuran (10 mL). The solution was added dropwise to the appropriate Grignard reagent (0.006 mol, 1 mol/L in tetrahydrofuran, prepared from respective bromide and magnesium) via a syringe at -40 C. After stirring for 20 min, the reaction was moved to ice-bath and quenched with saturated aqueous solution of ammonium chloride. The aqueous phase was extracted with dichloromethane and the combined organic layer was washed with brine, dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was dissolved in dichloromethane and treated with DDQ (0.004 mol). The reaction was refluxed for 3 h, filtered to move the precipitate. The crude product was further purified by column chromatography (petrol ether: ethyl acetate = 5:1) [21].

The synthetic route of 138526-69-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Ya-Nan; Feng, Yi-An; Li, Zhong; Shao, Xu-Sheng; Chinese Chemical Letters; vol. 28; 6; (2017); p. 1228 – 1231;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 17247-58-4, 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 17247-58-4 as follows.

A stirred solution of the ketimime 1a’ (50 g, 187.1 mmol, available from Aldrich Chemical Company, Milwaukee, Wis.) under N2 in dry THF (400 mL) was cooled to -78 C. and treated with 1 M solution of K-tBuO (220 mL, 1.15 equiv.) in THF. The reaction mixture was warmed to 0 C. and stirred for 1 h and treated with bromomethylcyclobutane (28 mL, 249 mmol). The reaction mixture was stirred at room temperature for 48 h and concentrated in vacuo. The residue was dissolved in Et2O (300 mL) and treated with aq. HCl (2 M, 300 mL) The resulting solution was stirred at room temperature for 5 h and extracted with Et2O (1 L). The aqueous layer was made basic to pH 12-14 with aq. NaOH (50%) and extracted with CH2Cl2 (3×300 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated to give pure amine (1b’, 18 g) as a colorless oil.

According to the analysis of related databases, 17247-58-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Schering Corporation; US2006/275366; (2006); A1;,
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. 556-96-7, name is 1-Bromo-3,5-dimethylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1-Bromo-3,5-dimethylbenzene

Preparation 9Preparation of (3,5-dimethyl-phenyl)-pyridin-2-yl-methanol.To a slurry of magnesium turnings (65.7 mg, 2.7 mmol) in THF (10 ml.) was added a crystal of iodine and a few drops of 1-bromo-3,5-dimethyl-benzene. The mixture was stirred at reflux temperature until the brown color started to disappear. The mixture was cooled to 0 0C, and the remaining 1-bromo-3,5-dimethyl-benzene (500 mg, 2.7 mmol) in THF was added dropwise. The reaction mixture was warmed to room temperature and was stirred until the magnesium was consumed. The reaction mixture was cooled to 0 0C, and pyridine-2-carboxaldehyde (289 mg, 2.7 mmol) in THF was added dropwise. The reaction mixture was stirred at room temperature for 30 min. The reaction was quenched with water, and the organic solution was extracted twice with ethyl acetate. The combined organic layers were washed sequentially with water and brine, and dried over MgSO4. The mixture was filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (0 – 50% ethyl acetate in heptane) to afford the title compound (440 mg, 76%). 1H NMR (400 MHz, CDCI3): delta 2.29 (s, 6 H), 5.21 (br s, 1 H), 5.68 (s, 1 H), 6.91 (s, 1 H), 6.98 (br. s, 2 H), 7.16-7.21 (m, 2 H), 7.60-7.63 (m, 1 H), 8.56-8.57 (m, 1 H); MS (ES+): 214.3 (M+1 ).

According to the analysis of related databases, 556-96-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; CAMERON, Kimberly O’Keefe; PERRY, David Austen; WO2010/67233; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 3344-70-5, The chemical industry reduces the impact on the environment during synthesis 3344-70-5, name is 1,12-Dibromododecane, I believe this compound will play a more active role in future production and life.

EXAMPLE 30 N, N’-Dodecane-1, 12-diyl-bis-isoquinolinium Dibromide (bIQDDB). 1, 12-Dibromododecane (mmol) was added to a solution (30 mL) of isoquinoline, and the solution heated for 24 hours at 65 C. The resulting precipitate was filtered, and the product washed five times with dry diethyl ether. The resulting off-white solid was isolated.’H NMR (300 MHz, DMSO-D6) S 10.06 (1H, d, C1-H), 8.78 (1H, d, C3-H), 8.58 (1H, d, C8-H), 8.48 (1H, d, C4-H), 8. 35 (1H, d, C7-H), 8.25 (1H, t, C5-H), 8.07 (1H, t, C6-H), 4.70 (2H, t, C’1-CH2), 2.0 (2H, m, C’2-CH2), 1.75 (1H, m, C’3-CH2), 1.15-1. 40 (7H, m, C’3-6-CH2).

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, 1,12-Dibromododecane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF KENTUCKY RESEARCH FOUNDATION; WO2005/66129; (2005); A2;,
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. 1347736-74-6, name is 4,7-Dibromo-5-fluoro-2,1,3-benzothiadiazole, A new synthetic method of this compound is introduced below., category: bromides-buliding-blocks

To 150 ml of ethanol was added 4,7-dibromo-5-fluoro-2,1,3-benzothiadiazole (4,7-dibromo-5-fluoro-2,1,3- Benzothiadiazole (5 g, 0.016 mol) was dissolved, and sodium borohydride (12.1 g, 0.32 mol) was added at 0 C And stirred at room temperature for 20 hours. After evaporating the solution, 160 ml of water were added and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and the residue was purified by silica column chromatography (hexane / ethyl acetate (25: 1)) to give 3,6-dibromo-4-fluoro

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; LG CHEM, LTD.; KIM, JIN-SEOK; LEE, JAE-CHOL; LEE, HANG-KEON; LIM, BO-GYU; (33 pag.)KR2017/50088; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 59907-13-0, These common heterocyclic compound, 59907-13-0, name is 2-Bromo-1-fluoro-3-methylbenzene, 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.

General procedure: Method A ( Buchwald-Hartwia ) To a mixture of C-1 (1 eq), BB-8 (1.3 eq) and sodium tert-butoxide (2 eq) in toluene (3 to 10 mL/mmol) under N2, was added BINAP (0.2 eq) and Pd2(dba)3 (0.1 eq). The rxn mixture was flushed with N2, heated at a given temperature and stirred for a given time (see Table 25). It was partitioned between water and EtOAc and the org. phase was washed with brine, dried over MgSC>4 and concentrated in vacuo. The crude was purified by CC using Hept/EtOAc. When necessary an additional purification by prep. LC-MS was performed.

Statistics shows that 2-Bromo-1-fluoro-3-methylbenzene is playing an increasingly important role. we look forward to future research findings about 59907-13-0.

Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; FROIDEVAUX, Sylvie; HUBLER, Francis; MURPHY, Mark; RENNEBERG, Dorte; STAMM, Simon; (188 pag.)WO2019/141803; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 556-96-7, name is 1-Bromo-3,5-dimethylbenzene, molecular formula is C8H9Br, 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

General procedure: To an oven-dried test tube equipped with a stir bar were added 0.01 mmol of Pd2(dba)3 and 0.03 mmol of ligand ((R)-Tol-BINAP or BrettPhos). Glove box was used to add 1.5 mmol ofNaOt-Pent and the tube was sealed with a Teflon screw cap. 1 mmol of aromatic halide,1.6 mmol of cyclopropylamine, and 2 mL of toluene were then added to the reaction mixture and heated at 80 C for 18 h. After completion, the reaction mixture was cooled to room temperature, diluted with diethyl ether, filtered over a short pad of silica gel, and concentrated in vacuum. Purification by flash chromatography on silica gel afforded N-cyclopropylaniline.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 556-96-7, its application will become more common.

Reference:
Article; Nguyen, Theresa H.; Maity, Soumitra; Zheng, Nan; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 975 – 980;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 103273-01-4, The chemical industry reduces the impact on the environment during synthesis 103273-01-4, name is 2-Bromo-4-(tert-butyl)aniline, I believe this compound will play a more active role in future production and life.

General procedure: A solution of 2-bromo-4-isopropylaniline 25a (36 g, 170 mmol) andN-benzyl-4-piperidone (31 mL, 170 mmol) in AcOH (130 mL) wastreated with TMSCN (22 mL, 180 mmol) at room temperature for 5 h.The reaction mixture was neutralized by 8 N aqueous NaOH (380 mL)at 0 C, and the mixture was extracted with AcOEt (500 mL). The organicphase was washed with saturated aqueous NaCl, dried (Na2SO4),filtered, and concentrated in vacuo. The residue was purified by silicagel column chromatography (AcOEt/hexane; 10:90 to 40:60) to affordcompound 26a (55 g, 79%) as a yellow solid.

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-4-(tert-butyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Arai, Yoshikazu; Katayama, Katsushi; Koda, Shuichi; Masumura, Makoto; Murata, Kenji; Muto, Tsuyoshi; Nagata, Tsutomu; Okada, Hiroyuki; Saito, Shoichi; Takashima, Kouhei; Yoshida, Ayako; Bioorganic and medicinal chemistry; vol. 28; 6; (2020);,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 103-64-0, These common heterocyclic compound, 103-64-0, name is (2-Bromovinyl)benzene, 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.

General procedure: A sealable vial equipped with a magnetic stir bar was charged with Cs2CO3 (325 mg, 1.0 mmol), Cu2O (3.5mg, 0.025 mmol) under a nitrogen atmosphere. The aperture of the vial was then covered with a rubber septum. Under a nitrogen atmosphere, alkyne (1, 0.75 mmol), vinyl halide (6, 0.5 mmol) and DMF (0.5 mL) were added by syringe. The septum was then replaced by a screw cap containing a Teflon-coated septum,and the reaction vessel was placed at 135 C. After stirring at this temperature for 12-24 h, the heterogeneous mixture was cooled to room temperature and diluted with ethyl acetate (20 mL). Theresulting solution was filtered through a pad of silica gel then washed with ethyl acetate (20 mL) and concentrated to give the crude material which was then purified by column chromatography on silica gel to yield enynes 7.

Statistics shows that (2-Bromovinyl)benzene is playing an increasingly important role. we look forward to future research findings about 103-64-0.

Reference:
Article; Tsai, Wan-Ting; Lin, Yun-Yung; Chen, Yi-An; Lee, Chin-Fa; Synlett; vol. 25; 3; (2014); p. 443 – 447;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 138526-69-9,Some common heterocyclic compound, 138526-69-9, name is 1-Bromo-3,4,5-trifluorobenzene, molecular formula is C6H2BrF3, 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.

-(3,4-Difluoro-5-morpholinophenyl)-N-(4-(3-methyl-leta-1,2,4-triazol-1- yl)phenyl)pyrimidin-2-amine Part I: 4-(5-Bromo-2,3-difluorophenyl)morpholine[0375] A mixture of 5-bromo-1,2,3-trifluorobenzene (2.5 g, 11.8 mmol), morpholine (1.0 rnL, 11.8 mmol), K2CO3 (1.6 g, 11.8 mmol) and DMSO (2 mL) in a sealed tube was heated up to 90C for 2.5 h. The reaction mixture was cooled to room temperature and diluted with water. The resulting colorless precipitate was filtered, washed with water, and dried in vacuo to afford 4-(5-bromo-2,3-difluorophenyl)morpholine in 76% yield. 1H NMR (CDCl3, 400 MHz) delta 6.91-6.87 (m, 1H), 6.75-6.72 (m, 1H), 3.80-3.78 (m, 4H), 3.04-3.02 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-3,4,5-trifluorobenzene, its application will become more common.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; WO2009/32861; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary