Carbon tetrabromide → HCID 86658324, compound

Participants

Reaction Conditions

Reaction Steps

At 0° C., 8.1 g (24.3 mmol) of carbon tetrabromide are added to a solution of 6.0 g (20.2 mmol) of N′-(diphenylmethylene)-4-hydroxy-2-methylbutane hydrazide and 6.3 g (24.3 mmol) of triphenylphosphane in 150 ml of dichloromethane. The reaction mixture is stirred at 0° C. for 1 h and then concentrated and purified by column chromatography on silica gel (cyclohexane/ethyl acetate). This gives 2.7 g (37%) of the desired product; (log P(HCOOH): 3.76); 1H-NMR (ppm): δ (DMSO-d6)=1.12 (d, 3H), 1.79-1.86 (m, 1H), 2.33-2.38 (m, 1H), 2.62-2.67 (m, 1H), 4.10-4.14 (m, 1H), 4.25-4.29 (m, 1H), 7.29-7.65 (m, 10H); LC-MS: m/z=359 [M+H]+.

Provenance & Evidence