Category: 133739-70-5

Application of 133739-70-5,Some common heterocyclic compound, 133739-70-5, name is 1-Bromo-2,3,5-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.

Dissolve trifluoromethanesulfonic acid 1- [4- (2-azepan-1-yl-ethoxy)-benzoyl]-6- methoxynaphthalen-2-yl ester (2.60 g, 6.53 mmol) in 200 ml. acetonitrile and add to this bis (pinacoloato) diboron (1.5 g, 7.96 mmol), bis (tricyclohexylphosphine) palladium (0) (0.72 g, 1.50 mmol) and cesium fluoride (7.33 g, 67.0 mmol). Heat the reaction to 100 C until LC/MS indicates all starting material is consumed. Add to this mixture 1-bromo- 2,3, 5-trifluorobenzene (2.00 g, 13.06 mmol) and another 720 mg of palladium catalyst and heat at 80 C for 24 hours. Filter the reaction, concentrate and purify on a silica gel column eluting with a 0-10% methanol/methylene chloride gradient to give 1.85 g (53%) of the title compound.

The synthetic route of 133739-70-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/73204; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 133739-70-5, A common heterocyclic compound, 133739-70-5, name is 1-Bromo-2,3,5-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.

A mixture of 17.28 g of methyl (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-(prop-2-ynyl)-piperidine-3-carboxylate in 173 cm3 of triethylamine is stirred for 5 minutes under an inert atmosphere at a temperature in the region of 20 C. 4.05 g of tetrakis(triphenylphosphine)palladium, 0.834 g of cuprous iodide and 7.9 g of 1-bromo-2,3,5-trifluorobenzene are added.The mixture is stirred for 2 hours at a temperature in the region of 80 C. After cooling to approximately 20 C., 150 cm3 of ethyl acetate and 150 cm3 of water are added to the reaction mixture, which is then separated after settling out.The aqueous phase is extracted with 3 times 150 cm3 of ethyl acetate.The organic phases are pooled, washed with 5 times 150 cm3 of water, dried over sodium sulfate, filtered, and concentrated under reduced pressure (5 KPa) at a temperature in the region of 40 C. The residue obtained is purified by chromatography under a nitrogen pressure of 50 KPa, on a column of silica gel (particle size 20-45mu; diameter 7 cm; 600 g), eluding with pure ethyl acetate and collecting first a fraction of 2.5 1, and then fractions of 250 cm3.Fractions 2 to 29 are pooled and then concentrated as above. 18.4 g of methyl (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]-piperidine-3-carboxylate, in the form of a yellow oil, are obtained. [0293] 1H NMR spectrum (400 MHz, (CD3)2SO d6, delta in ppm): from 1.55 to 1.95 (mt: 5H); 2.39 (mt: 1H); 2.58 (broad d, J=10 Hz: 1H); 2.68 (mt: 1H); 2.82 (mt: 1H); 2.91 (mt: 1H); 3.09 (mt: 1H); 3.23 (mt: 1H); 3.58 (s: 3H); 3.61 (s: 2H); 3.88 (s: 3H); 7.31 (mt: 1H); 7.49 (dd, J=9 and 2.5 Hz: 1H); from 7.55 to 7.65 (mt: 1H); 7.73 (d, J=2.5 Hz: H); 7.92 (d, J=4.5 Hz: 1H); 8.02 (d, J=9 Hz: 1H); 8.89 (d, J=4.5 Hz: 1H).

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; Bacque, Eric; Bigot, Antony; Ahmad, Youssef Ei; Malleron, Jean-Luc; Mignani, Serge; Ronan, Baptiste; Tabart, Michel; Viviani, Fabrice; US2004/87619; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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 133739-70-5 as follows. COA of Formula: C6H2BrF3

A solution of butyllithium (0.10 mol) in hexane was dropped in a mixture of 2,3,5-trifluoro-1-bromobenzene (0.10 mol) and THF 100 ml with maintaining a temperature of -78 C. and the mixture formed was stirred for 30 minutes at the same temperature. To this solution was dropped a solution of 4-pentylcyclohexanone (0.11 mol) in THF (50 ml) with maintaining a temperature of -78 C., the mixture formed was warmed up gradually to room temperature with stirring and stirred for 2 hours at room temperature. The reaced product was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. After the solvent was distilled off, toluene (100 ml) and p-toluenesulfonic acid (5 g) was added to the residue and then the mixture formed was heat-refluxed with dehydration of water formed. After cooling, the organic phase was washed enough with water and then dried over anhydrous magnesium sulfate. After the solvent was distilled off, ethanol (80 ml) and Raney nickel (3 g) were added to the residue and the mixture was stirred for 12 hours under hydrogen atmosphere. After it was confirmed that absorption of hydrogen was stopped, the catalyst was removed from the reaction system by filtration. The solvent was distilled off to give 1,2,5-trifluoro-4-(4-pentylcyclohexyl)benzene (89 mmol) in the form of oil as residue. This product was a mixture of cis/trans, however it was used in the subsequent reaction without purification.

According to the analysis of related databases, 133739-70-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chisso Corp.; US6117361; (2000); A;,
Bromide – Wikipedia,
bromide – Wiktionary