Tetrahydrofuran → 5-Bromo-1-(5-phenyl-2-thienylmethyl)-2-trifluoromethylbenzene

To a mixed solution of the above 5-bromo-2-trifluoromethylphenyl 5-phenyl-2-thienyl ketone (670 mg) in methanol (20 ml)-tetrahydrofuran (10 ml) was added sodium borohydride (62 mg), and the mixture was stirred at room temperature for 3 hours. The solvent was evaporated under reduced pressure, and the residue was dissolved in chloroform (10 ml)-acetonitrile (20 ml). Thereto was added triethylsilane (0.78 ml), and the mixture was cooled to 0° C. Thereto was added dropwise boron trifluoride.diethyl ether complex (0.52 ml). The mixture was stirred at room temperature for 45 minutes, and added thereto was a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane) to give the desired 5-bromo-1-(5-phenyl-2-thienylmethyl)-2-trifluoromethylbenzene (565 mg) as colorless oil.

1. customThe solvent was evaporated under reduced pressure
2. dissolutionthe residue was dissolved in chloroform (10 ml)-acetonitrile (20 ml)
3. additionThereto was added triethylsilane (0.78 ml)
4. temperaturethe mixture was cooled to 0° C
5. additionThereto was added dropwise boron trifluoride
6. stirringThe mixture was stirred at room temperature for 45 minutes
7. additionadded
8. extractionthe mixture was extracted with ethyl acetate
9. washThe extract was washed with brine
10. dry with materialdried over sodium sulfate
11. customThe solvent was evaporated under reduced pressure
12. customthe residue was purified by silica gel column chromatography (hexane)

ORD record

ord-75b1130cbfcc427498664511a4c837e5

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08785403B2