Tetrahydrofuran → 5-Bromo-2-iodobenzaldehyde

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Reaction Steps

To 5-bromo-2-iodobenzonitrile (7.49 g, 24.2 mmol) in tetrahydrofuran (40 mL) at −78° C. was added diisobutylaluminum hydride (1.0M in hexanes; 24.2 mL, 24.2 mmol) over 5 minutes, and the reaction was allowed to warm to room temperature and monitored by analytical TLC. After stirring overnight at room temperature, starting material was still present, so the mixture was cooled to 0° C. and additional diisobutylaluminum hydride (1.0M in hexanes; 10.0 mL, 10.0 mmol) was added. After stirring for 2 hours at room temperature, no starting material was seen by analytical TLC, so the mixture was carefully quenched with freshly saturated aqueous sodium sulfate and diluted with ethyl acetate. The mixture was stirred vigorously for 1 hour and then filtered through Celite. The filtrate was concentrated, and the resulting oil solidified on standing. The solid was stirred vigorously in dichloromethane and 1N aqueous hydrochloric acid, and the aqueous layer was separated and extracted with dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated to give the title compound.

Provenance & Evidence