Sodium Iodide → (2-(4-Bromophenoxy)ethyl)dimethylamine

Participants

Reaction Steps

A mixture of 4-bromophenol (5.0 g, 28.9 mmol), 2-(N,N-dimethylamino)ethyl chloride, hydrochloride (6.24 g, 43.4 mmol), sodium iodide (600 mg, 4 mmol), cesium carbonate (28 g, 86.7 mmol) and methyl ethyl ketone (120 ml) was heated to reflux for 4 h. After cooling to r.t., the mixture was filtered and washed with acetone. The combined filtrates were concentrated in vacuo, and the residue was chromatographed on silica gel (dichloromethane/methanol 95:5 to 90:10) to give a pale yellow liquid. Bulb-to-bulb distillation (80-84° C./0.05 mmHg) afforded the title compound (5.19 g, 74%) as a colorless liquid.

Provenance & Evidence