Water → 1-Bromo-3-(2,2-diethoxyethoxy)benzene

Participants

Reaction Steps

To a solution of 3-bromophenol (1.68 g, 9.77 mmol) in N,N′-dimethylformamide (32 mL), sodium hydride (purity 50%) (516 mg, 10.7 mmol) was added under ice-cold conditions, and bromoacetaldehyde diethylacetal (1.76 mL, 11.7 mmol) was added at 0° C., and the resultant mixture was stirred at 120° C. overnight. The reaction solution was added with water at room temperature and extracted with diethyl ether. The organic layer was washed with brine, dried over anhydrous sodium sulfate, concentrated in vacuo, and purified using silica-gel column chromatography (hexane). 1-Bromo-3-(2,2-diethoxyethoxy)benzene (2.69 g. yield >100%) was obtained as a yellow oil.

Provenance & Evidence