Phenol → 3-Bromodiphenyl ether

Participants

Reaction Steps

To a solution of phenol (5.08 g; 54 mmol) in 30 ml dry DMF at 0 C. was added portionwise NaH (1.98 g; 66 mmol; 80% dispersion in oil). The mixture was stirred 30 min at r.t. then 1,3-dibromobenzene (33 ml; 273 mmol) and Cu2O (3.95 g; 28 mmol) were added. The final mixture was heated to reflux for 4 h, cooled to r.t., diluted with Et2O (200 ml), washed with water (3×200 ml), NaOH (1.0 M; 2×100 ml) and brine, dried over MgSO4 and concentrated. Flash chromatography with hexane afforded the desired material.

Provenance & Evidence