Triphenylphosphine → 1-Benzyl-3-(bromomethyl)-1H-indazole

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 550 mg (2.09 mmol, 1.3 equiv) of triphenylphosphine in 10 mL of acetonitrile at 0° C. is added 0.1 mL (1.93 mmol, 1.2 equiv) of Br2. The resulting orange-yellow suspension is stirred 10 min at 0° C., then a solution of 383 mg (1.61 mmol) of (1-Benzyl-1H-indazol-3-yl) methanol, prepared as in Intermediate 15, in 5 mL of acetonitrile is added over 2 min. The resulting solution is stirred 1 h at RT, and the solvent is removed in vacuo. Purification of the residue by silica gel flash column chromatography using hexane/EtOAc 5/1 as eluent afforded 305 mg of the title compound as a white solid: 1H NMR (CDCl3, 300 MHz) δ7.82 (d, 1H), 7.40-7.16 (m, 8H), 5.59 (s, 2H), 4.90 (s, 2H); Rf =0.75 in hexane/EtOAc 2/1.

Provenance & Evidence