Anisole → 4-Bromoanisole

The bromination of anisole with one equivalent of bromine is chloroform, at room temperature, is reported to give an 80% yield of monobromoanisole. Grignard, Bellet and Courtot, Ann. Chim. 4, 28 (1915). The preparation of dibromoanisole from anisole, and of tribromoanisole from dibromoanisole, in carbon tetrachloride, is also reported. Kohn and Sussman, Monatsh. Chem. 46, 575 (1925). "Several days" reaction time is reported for the preparation of several tribromophenyl alkyl ethers. Yields are not reported. Baiford and Birosel, J. Am. Chem. Soc., 51, 1776 (1929). The bromination of anisole with three equivalents of bromine yields 1.5% tribromoanisole. Similarly, the bromination of monobromoanisole with two equivalents of bromine in chloroform is reported to give only small quantities of tribromoanisole, and tribromoanisole is reported not to brominate further. D. M. Birosel, Univ. Phillipines Natural Applied Sci. Bull. 1, 145 (1931).