Carbon tetrabromide → 4-Bromo-1-(bromomethyl)-2-chlorobenzene

Participants

Reaction Steps

To a magnetically stirring solution of (4-bromo-2-chloro-phenyl)-methanol (2.80 g, 12.67 mmol) from step 1 above in CH2Cl2 (60.0 mL) under argon at 0° C., was added carbon tetrabromide (4.41 g, 13.30 mmol) followed by triphenylphosphine (3.48 g, 13.30 mmol). The resulting mixture was stirred for 4 hours at room temperature. The resulting reaction mixture was concentrated in vacuo and the crude residue was purified by flash column chromatography (10% EtOAc in Hexanes) to yield the intermediate bromide as a clear oil (3.59 g, 100%). 1H NMR (400 MHz, CDCl3): δ 4.53 (s, 2H), 7.29 (d, J=8.2 Hz, 1H), 7.39 (dd, J=8.2, 1.9 Hz, 1 H), 7.56 (d, J=1.9 Hz, 1H).

Provenance & Evidence