N-bromobutanimide → 4-Bromo-2-(6-carboxyhexyl)cyclopent-2-en-1-one

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 35.9 g. (0.171 moles) of 2-(6-carboxyhexyl) cyclopent-2-en-1-one [Bagli et al., Tetrahedron Letters, No. 5, 465 (1966)], 35.0 g. (0.197 moles) of N-bromosuccinimide, and 600 ml. of carbon tetrachloride is refluxed for 35 minutes. The mixture is cooled to 5°C. and filtered. The filtrate is washed with cold water, dried over magnesium sulfate, and taken to dryness to give an oil, λMeOHmax. = 225 mμ (8850); νmax. = 1705 (carbonyl groups) and 1625. cm-1 (olefin group).

Provenance & Evidence