Hydrochloric Acid → 1-(5-Bromo-[1,1'-biphenyl]-2-yl)-2,2,2-trifluoroethanol

Temperature

0 °C

To a solution of 5-bromo-[1,1′-biphenyl]-2-carbaldehyde (1.9 g, 7.3 mmol) and was added TMSCF3 (1.2 g, 8.7 mmol) in THF (20 mL) and cooled to 0° C. To this solution was added TBAF (1.46 mL, 1M in THF) and the reaction mixture was warmed to RT for 3 h. After this time, the mixture was treated with 3 N HCl (5 mL) and stirred for 12 h. Then the reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered, concentrated in vacuo and purified by normal phase silica gel column (EtOAc:PE=1:10) to afford 1-(5-bromo-[1,1′-biphenyl]-2-yl)-2,2,2-trifluoroethanol as a colorless oil.

1. temperaturethe reaction mixture was warmed to RT for 3 h
2. extractionextracted with ethyl acetate
3. washThe combined organic layers were washed with brine
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. custompurified by normal phase silica gel column (EtOAc:PE=1:10)

ORD record

ord-8f7da66d5a9548858237e03e2a8ca154

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09199994B2