Phosphonium, (bromomethyl)triphenyl-, bromide (1:1) → (Z)-2-(2-bromovinyl)-6-fluoroquinoline

Participants

Reaction Steps

To as suspension of (bromomethyl)triphenylphosphonium bromide (14.94 g, 34.3 mmol) in 100 mL of THF was added potassium tert-butoxide (3.84 g, 34.3 mmol) portionwise under Ar. Then the reaction mixture was stirred for 1 h at this temperature. 6-Fluoroquinoline-2-carbaldehyde (5 g, 28.5 mmol) in 40 mL of THF was added. The resulting reaction mixture was stirred for 5 h at −75° C. and allowed to warm up overnight. The reaction mixture was diluted with petrol ether and the solid was sucked off. The mother liquid was concentrated, diisopropyl ether was added and the formed precipitate was sucked off. The mother liquid was purified by column chromatography (cyclohexane/EA) to give 4.7 g (65.3%) of the title compound as brown solid. LC-MS: m/e 254.0.

Provenance & Evidence