Diisobutylaluminumhydride → [3,5-Dibromo-4-(bromomethyl)phenyl]methanol

Participants

Reaction Conditions

Reaction Steps

A solution of 3,5-dibromo-4-bromomethyl-benzoic acid methyl ester (57) (5.2 g, 13.44 mmol) in tetrahydrofuran (50 mL) at 0° C. was treated with a 1M solution of diisobutylaluminum hydride in tetrahydrofuran (30 mL, 30 mmol). The reaction mixture was stirred for 2 h at 0° C. TLC revealed starting material was still present. Additional 1M solution of diisobutylaluminum hydride in tetrahydrofuran (16 mL, 16 mmol) was added at 0° C. and the reaction mixture was stirred for 30 min at 0° C. The reaction was quenched cautiously by pouring it onto a mixture of ice and concentrated hydrochloric acid (100 mL) and the mixture was extracted with ethyl acetate (3×150 mL). The organic layers were combined, dried with magnesium sulfate, filtered, and concentrated under vacuum to afford a solid which was dried under high vacuum to afford (3,5-dibromo-4-bromomethyl-phenyl)-methanol (58) (4.56 g, 94%) as an off-white solid; LRMS-EI(+) for C8H7Br3O (M+) m/z=356. MW=358.8564, Exact Mass=355.8047

Provenance & Evidence