p-Bromoacetophenone → 1-[4-(4-fluorophenoxy)phenyl]ethanone

Participants

Reaction Steps

The starting material was prepared as follows. An Ullmann reaction using p-fluorophenol and p-bromoacetophenone gave 4'-(4-fluorophenoxy)acetophenone, m.p. 65°-67°C. This was subjected to the Willgerodt reaction using morpholine and sulfur, followed by hydrolysis, to give crude 4-(4-fluorophenoxy)phenylacetic acid, which was esterified and gave ethyl 4-(4-fluorophenoxy)phenylacetate, b.p. 139°-142°C./0.3 mm. This ester was treated conventionally with diethyl carbonate and sodium ethoxide, and then with dimethyl sulfate, to yield the required ethyl 2-[4-(4-fluorophenoxy)phenyl]-2-methylmalonate, b.p. 174°-182°C./0.7 mm.

Provenance & Evidence