Ethyl 4-iodobenzoate → 4-Iodobenzyl alcohol

Participants

Reaction Conditions

Reaction Steps

A stirred, cooled (−78° C.) solution of ethyl-4-iodo-benzoate (available from Lancaster, 12.9 g, 45 mmol) in anhydrous dichloromethane (100 mL) under argon was treated with a 1M solution of di-isobutyl aluminum hydride in dichloromethane (100 mL, 100 mmol). The reaction mixture was allowed to warm to 0° C. in 1.5 h, quenched with saturated aqueous ammonium chloride solution and the resulting emulsion was filtered over a bed of celite. The phases in the filtrate were separated and the aqueous phase was extracted with dichloromethane (×1). The combined organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford the title product as a white solid (9 g, 85%).

Provenance & Evidence