Carbon tetrabromide → 4-nitro-2-(trifluoromethoxy)benzyl bromide

Participants

Reaction Conditions

Reaction Steps

Add (4-bromo-2-(trifluoromethoxy)phenyl)methanol (9.757 g, 36 mmol) and dichloromethane (180 mL) to a 500 mL flask equipped with a magnetic stir bar and N2 inlet. Cool the solution to 0° C. and then treat with triphenylphosphine (11.33 g, 43 mmol) and carbon tetrabromide (14.26 g, 43 mmol). Stir the reaction at 0° C. for 45 minutes, warm to room temperature and stir an additional 1 hour. Wash the reaction with water (2×180 mL) and saturated sodium chloride solution (1×180 mL), then dry over anhydrous magnesium sulfate. Filter through Celite® and concentrate under vacuum to dryness. Dissolve the residue in hexanes, filter to remove the triphenyl phosphine oxide, and concentrate to a colorless oil. Purify the crude product via silica gel chromatography eluting with hexanes to afford 10.5 g (88%) of the product as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 7.46-7.40 (m, 2H), 7.38-7.33 (m, 1H), 4.46 (s, 3H).

Provenance & Evidence