Diethyl Ether → 1-Bromo-4-(methoxymethoxy)benzene

Participants

Reaction Steps

5.2 g (30 mmol) of 4-bromophenol was dissolved in 20 ml of anhydrous methylene chloride, and 1.6 g (5.9 mmol) of tetrabutylammonium chloride and 20 ml (50 mmol) of 2.5N sodium hydroxide solution were added successively under ice cooling and stirring. Further, 3.4 ml (45 mmol) of chloromethyl methyl ether was added, and the mixture was brought back to room temperature and stirred for 30 minutes. After the reaction, diethyl ether was added to the reaction solution to carry out extraction, and the organic layer was washed successively with water, 1N sodium hydroxide solution, saturated saline, saturated ammonium chloride solution and saturated saline, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Thereby, 5.7 g of 4-methoxymethoxybromobenzene was obtained as a colorless oil (yield 87%).

Provenance & Evidence