Benzyl Bromide → 3-Phenyl-2,2-bis(3-(trifluoromethoxy)phenyl)propanenitrile

To a solution of diisopropyl amine (2.48 mL, 17.5 mmol) in THF (60 mL) at −78° C. was added dropwise n-BuLi (1.6 M in hexane, 11.5 mL, 18.3 mmol) and the reaction mixture was stirred for 5 min. A solution of (2,2-bis(3-(trifluoromethoxy)phenyl)acetonitrile (5.51 g, 15.3 mmol), prepared as described in Procedure 14, in THF (5 mL) was added dropwise to the reaction mixture and stirred for 1 h. Benzyl bromide (2.17 mL, 18.3 mmol) was added dropwise, then the cooling bath was removed and the reaction mixture was stirred at rt for 45 min. The reaction mixture was poured into H2O (75 mL) and extracted with diethyl ether (2×75 mL). The combined organic portions were dried over Na2SO4, filtered and concentrated under reduced pressure to yield a residue. The residue was purified on a silica gel ISCO cartridge with elution at 5 to 15% Et2O/hexane to give 3-phenyl-2,2-bis(3-(trifluoromethoxy)phenyl)propanenitrile (6.75 g, 98% yield) as a clear yellow oil.

1. additionwas added dropwise to the reaction mixture
2. stirringstirred for 1 h
3. customthe cooling bath was removed
4. stirringthe reaction mixture was stirred at rt for 45 min
5. additionThe reaction mixture was poured into H2O (75 mL)
6. extractionextracted with diethyl ether (2×75 mL)
7. dry with materialThe combined organic portions were dried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customto yield a residue
11. customThe residue was purified on a silica gel ISCO cartridge with elution at 5 to 15% Et2O/hexane

ORD record

ord-e92e0028a5ca46a69992f6a78517ec20

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08404896B2