Phenol → 3-Bromodiphenyl ether

Participants

Reaction Steps

To a stirred mixture of 23 g sodium methylate in 69 g methanol and 200 ml of 2-methoxyethyl ether (diglyme) at room temperature was added dropwise 40.0 g of phenol in a period of 1/2 hour. The reaction mixture was then heated to 165°, and 5.0 g cuprous bromide was added. The reaction mixture was cooled to 150° and 100.0 g of 1,3-dibromobenzene was added rapidly. Upon complete addition, the reaction mixture was warmed to 165° and stirred for 24 hours. The reaction mixture was then allowed to cool to room temperature and filtered. The filter cake was washed with two 75 ml portions of chloroform. The filtrate was dried with sodium sulfate and filtered. Chloroform was evaporated from the filtrate under reduced pressure, leaving a residue. The residue was distilled under reduced pressure to give 40.5 g of 1-bromo-3-phenoxybenzene; bp, 98°-100°/0.5 mm. The nmr and the ir spectra were consistent with the assigned structure.

Provenance & Evidence