Triphenylphosphine → 1-Benzyl-3-bromomethyl-4,5,6,7-tetrahydro-1H-indazole

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 752 mg (2.87 mmol, 1.3 equiv) of triphenylphosphine in 10 mL of CCl4 at 0° C. is added 135 μL (2.63 mmol, 1.2 equiv) of Br2. The resulting orange-yellow suspension is stirred 10 min at 0° C., then a solution of 580 mg (2.39 mmol) of (4,5,6,7-Tetrahydro-1-benzyl-1H-indazol-3-yl) methanol in 3 mL of CCl4 is added over 2 min. The resulting solution is stirred 2.5 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 76 mg of the title compound as a clear oil: 1H NMR (CDCl3, 300 MHz) δ7.32-7.24 (m, 3H), 7.10 (m, 2H), 5.17 (s, 2H), 4.49 (s, 2H), 2.48 (m, 4H), 1.74 (m, 4H); low resolution MS (FAB)m/e 305 (MH+).

Provenance & Evidence