Triphenylphosphine → 2-Bromomethyl-3-phenyl-1-(toluene-4-sulfonyl)-1H-indole

Participants

Reaction Steps

To a solution of [3-phenyl-1-(toluene-4-sulfonyl)-1H-indol-2-yl]methanol (1.31 g, 3.47 mmol) and triphenylphosphine (1.09 g, 4.16 mmol) in DCM (30 mL) at RT under a nitrogen atmosphere was added NBS (240 mg, 4.16 mmol) and stirring was continued for 2 h. Volatiles were removed under reduced pressure and the resulting residue was purified by column chromatography (Si—PCC, gradient 30-100% DCM in pentane) affording 2-Bromomethyl-3-phenyl-1-(toluene-4-sulfonyl)-1H-indole as a gum (440 mg, 29%). 1H NMR (CDCl3, 400 MHz): δ 8.16 (1H, dt, J=8.48, 0.84 Hz), 7.92-7.88 (2H, m), 7.60-7.49 (4H, m), 7.48-7.37 (3H, m), 7.28-7.22 (3H, m), 5.05 (2H, s), 2.38 (3H, s).

Provenance & Evidence