Hexamethylphosphoramide → 1-(4-Bromophenyl)pent-1-ene

Participants

Reaction Conditions

Reaction Steps

52 ml (83.2 mmols) of a 1.6M n-butyllithium solution in hexane are added to a suspension, cooled to -10° C., of 34 g (85.1 mmols) of n-butyltriphenylphosphonium bromide in 150 ml of tetrahydrofuran. After 20 minutes' reaction, the whole is cooled to -80° C. and 50 ml of hexamethylphosphoric triamide are added, as well as 10 g (54 mmols) of 4-bromobenzaldehyde dissolved in 40 ml of tetrahydrofuran. After returning to room temperature and hydrolysis with a saturated ammonium chloride solution, the reaction mixture is extracted with ether. Customary treatment of the organic phase yields 10 g of the expected compound after purification by chromatography on a silica column (eluent: petroleum ether).

Provenance & Evidence