p-Toluenesulfonic acid → 1-Bromo-2-(1E)-1-propen-1-ylbenzene

Participants

Reaction Steps

p-Toluenesulfonic acid (30 mg) was added to a solution (50 mL) of 1-(2-bromophenyl)-1-propanol (5.55 g, 3.0 mmol) in toluene, followed by reflux for 5 hours. Next, the reaction solution was added to a saturated aqueous solution of sodium bicarbonate under ice-cooling to neutralize the reaction solution, and the mixture was then extracted with diethyl ether. After the extract was washed with a saturated brine and then dried over sodium sulfate, the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (developed with diethyl ether/hexane=1/10) to give 2-((E)-1-propenyl)bromobenzene (4.75 g, yield 100%).

Provenance & Evidence