Diisobutylaluminum hydride → (3-Bromo-2-(bromomethyl)phenyl)methanol

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 3-bromo-2-(bromomethyl)benzoate in dry toluene (0.45 M) was added dropwise to a solution of DIBAL-H (2 eq., 1 M in toluene) in dry toluene (0.9 M) at 0° C. The reaction mixture was stirred at 0° C. for 2 h. Then, the reaction mixture was quenched with a solution of 1N HCl until pH 1 and the mixture was extracted with EtOAc. The combined organic extracts were washed with brine and dried (Na2SO4). Evaporation of the solvent yielded (96%) the title compound as a white powder, which was used in the next step without further purification. 1H NMR (300 MHz, DMSO-d6, 300K) δ 7.66 (1H, d, J=8.0 Hz), 7.56 (1H, d, J=7.4 Hz), 7.32 (1H, t, J=7.6 Hz), 5.51 (1H, bt, J=5.4 Hz), 4.83 (2H, s), 4.70 (2H, bd, J=4.6 Hz).

Provenance & Evidence