Diisobutylaluminum hydride → 3-Bromo-4-iodobenzenemethanol

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 3-bromo-4-iodobenzoate (Preparation 23, 4.3 g, 12.6 mmol) in CH2Cl2 was cooled, under N2, to −78° C. DIBAL-H was added slowly to the solution, which was stirred at −78° C. for 45 minutes and then allowed to come to room temperature. Next, the reaction mixture was diluted with 1M HCL (40 mL) and stirred for 30 minutes. The reaction was further diluted with water and extracted with CH2Cl2. The organic phase was dried (Na2SO4) and concentrated under vacuum to afford the intermediate (3.2 g, 82%) as a solid. 1HNMR (CDCl3): 7.85 (1H), 7.67 (1H), 7.02 (1H), 4.65 (2H), 1.76 (1H, OH).

Provenance & Evidence