N-bromobutanimide → Methyl 2'-(bromomethyl)-[1,1'-biphenyl]-4-carboxylate

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Reaction Steps

A 5 L three-necked 24/40 round-bottom flask equipped with a mechanical stirrer, a reflux condenser with a nitrogen inlet at the top, and a thermometer was charged with 53.42 g (0.204 mol) of 2'-methylbiphenyl-4-carboxylic acid methyl ester, 3.4 L carbon tetrachloride, 38.09 g (0.214 mol) of N-bromosuccinimide and 2.0 g of 2,2'-azobis(2-methylpropionitrile). The flask was degassed and flushed with nitrogen, the stirrer was started and the contents were refluxed for 5 hours. The reaction mixture was then cooled to room temperature, filtered and evaporated. The residual oil was purified by recrystallization from dichloromethane-hexane to afford 48.48 g (78%) of the product which had: mp 80°-81° C.; NMR (CDCl3) δ3.94 (s, 3H), 4.40 (s, 2H), 7.20-7.26 (m, 1H), 7.32-7.41 (m, 2H), 7.48-7.54 (m, 3H), 8.12 (d, J=12 Hz, 2H); MS (EI) m/e 304, 306 (M+). Anal. (C15H13BrO2) C, H.

Provenance & Evidence