N-bromobutanimide → 2-[4-(Bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol

Participants

Reaction Steps

1,1,1,3,3,3-Hexafluoro-2-p-tolylpropan-2-ol (387 mmol, 100 g) was dissolved in carbon tetrachloride (400 mL) and N-bromosuccinimide (387 mmol, 68.9 g) was added in one portion followed by 2,2′-azobis(isobutyronitrile) (0.387 mmol, 0.064 g). The reaction was stirred at reflux for 4 hours, filtered through dicalite and the filtrate was evaporated to leave crude oil. The crude oil was triturated with diethyl ether, the solid obtained was filtered off and the filtrate taken to dryness (3 times) to yield the title compound as an oil (138 g). 1H NMR (CDCl3, 400 MHz): δ 4.49 (2H, s), 7.49 (2H, d), 7.69 (2H, d)

Provenance & Evidence