N-bromobutanimide → Methyl 2-[2-(bromomethyl)phenyl]-2-oxoacetate

Participants

Reaction Steps

5.34 g (30 millimoles) of methyl 2-methylphenylglyoxylate and 5.34 g (30 millimoles) of N-bromosuccinimide in 1,000 1 of tetrachloromethane are exposed for one hour to a 300 W Hg vapor lamp. Thereafter, the organic phase is washed once with water and three times with sodium bicarbonate solution and dried over sodium sulfate/sodium carbonate. After the organic phase has been evaporated down, the crude product is chromatographed over silica gel using 1:9 methyl tert-butyl ether/n-hexane. 3.8 g (49%) of the abovementioned compound are obtained as a yellow oil. 1H-NMR (CDCl3): δ=3.97 (s, 3H); 4.90 (s, 2H); 7.4-7.8 (m, 4H)

Provenance & Evidence