Benzene, 1-iodo-3-methoxy- → 1-(Bromomethyl)-2-iodo-4-methoxybenzene

Participants

Reaction Steps

Bromomethyl methyl ether (5.14 ml, 63.2 mmol) was added to a solution of 3-iodoanisole 19 (7.4 g, 31.6 mmol) in glacial acetic acid (17.0 mL) and the colorless solution was stirred for 2 days at room temperature as set forth in T. J. McCord, D. E. Thornton, K. L. Hulme and A. L. Davis, “Synthesis and Microbiological Properties of 2-Iodotyrosine and Related Compounds.” Texas J. Sci., 30, pp 357-363 (1978). The reaction mixture was diluted with water and then extracted with ethyl acetate. The organic phase was dried over Na2SO4, filtered and evaporated to produce a yellow oil which was purified by silica gel column chromatography to yield 1-bromomethyl-2-iodo-4-methoxybenzene (20) as a white solid (4.59 g, 45%).

Provenance & Evidence