4-Bromoanisole, from anisole with

The reaction of anisole with copper(II) bromide in benzene at 50°C yielded no detectable products after 10 h. In contrast, in a similar reaction using alumina-supported copper(II) bromide, p-bromoanisole in 90 % yield was obtained from the reaction run at 30°C for 2 h. (eqn. 1). No dibromides were detected. 

The checkers have prepared the following bromides by the same procedure w-chlorobromobenzene (b.p. 191-194°) from jw-chloroaniline in 91-94% yields ra-dibromobenzene (b.p. 215-217°) from ra-bromoaniline in 80 87% yields and u-bromo-anisole (b.p. 114-116°/29 mm.) from o-anisidine in 88-93% yields. In the preparation of o-bromoanisole the washing with sulfuric acid was omitted. 

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