N-bromobutanimide → (R)-2-[2-(2-bromomethylphenyl)-2-methylpropyl]-2-trifluoromethyloxirane

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (R)-2-[2-(2-methylphenyl)-2-methylpropyl]-2-trifluoromethyloxirane (37 g, 0.143 mmol) in 500 mL of anhydrous CCl4 at room temperature was added N-bromosuccinimide (26 g, 0.146 mmol). The reaction mixture was heated to 70° C. and the reaction flask was irradiated with a UV light (500 W) for 1 hour. The reaction mixture, after cooling to normal room temperature, was washed with saturated aqueous sodium bicarbonate solution followed by water, dried over anhydrous sodium sulfate, and the solvent evaporated in vacuo to give (R)-2-[2-(2-bromomethylphenyl)-2-methylpropyl]-2-trifluoromethyloxirane as a light yellow oil (46.6 g, 81%; ˜85% pure) which was used for the next reaction without purification.

Provenance & Evidence