Triphenylphosphine → 3-(Bromomethyl)-1-benzofuran

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 912 mg (3.48 mmol, 1.2 equiv) of triphenylphosphine in 5 mL of CCl4 at 0° C. is added 165 μL (3.19 mmol, 1.1 equiv) of Br2. The resulting orange-yellow suspension is stirred 10 min at 0° C., then a solution of 430 mg (2.90 mmol) of 3-hydroxymethylbenzofuran, prepared as in Intermediate 19, in 5 mL of CCl4 is added over 2 min. The resulting solution is stirred 1.5 h at RT, and the solvent is removed in vacuo. Purification of the residue by silica gel flash column chromatography using hexane/EtOAc 20/1 as eluent afforded 500 mg of the title compound as a clear, colorless oil: 1H NMR (CDCl3, 300 MHz) δ7.71 (m, 2H), 7.50 (m, 1H), 7.37 (m, 2H), 4.62 (s, 2H); Rf =0.67 in hexane/EtOAc 5/1.

Provenance & Evidence