Azobisisobutyronitrile → HCID 19988394, compound

Participants

Reaction Steps

2,5-Dihydro-4-methyl-2-oxo-3-phenylfuran, (U.S. Pat. No. 3,622,569), (355 g) in carbon tetrachloride (50 mls) and N-bromosuccinimide (3.85 g) were heated under reflux in the presence of 2,2'-azobisisobutyronitrile (AIBN) (cat.quantity) and a 150W lamp. After 1 h a pale yellow solution was formed accompanied by the presence of succinimide. T.l.c. analysis showed a mixture of products. After filtration, and removal of solvent, the residue was purified by flash chroma-tography on silica gel eluting with 10% ethyl acetate/hexane. The title compound was obtained as a viscous yellow oil, (3.53 g, 68%), (Found; M+, 251.9802. C11H9O2Br requires M, 251.9786); νmax 1780(s) and 1650(w)cm-1 ; δH (CDCl3) 2.28 (3H,s), 6.80 (1H,s) and 7.45 (5H,m).

Provenance & Evidence