N-bromobutanimide → HCID 12026771, compound

Participants

Reaction Steps

A mixture of methyl 5-tert-butyl-2-methylfuran-3-carboxylate (10.4 g, 53 mmol), N-bromosuccinimide(9.9 g, 55 mmol), and azobisisobutyronitrile (0.1 g, 0.6 mmol) in carbon tetrachloride (100 mL) was heated to reflux for 1.5 h. The suspension was cooled to room temperature, and succinimide was removed by filtration and rinsed with carbon tetrachloride. The combined filtrates were evaporated to dryness. The residue was subjected to Kugelrohr distillation (<1 mbar, 110-120° C.) to yield methyl 5-tert-butyl-2-(bromomethyl)furan-3-carboxylate (14.3 g, 98% yield) as a light-yellow oil. 1H-NMR (300 MHz, CDCl3): δ 6.28 (s, 1H), 4.80 (s, 2H), 3.85 (s, 3H), 1.28 (s, 9H) ppm.

Provenance & Evidence