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

Reaktionsgleichung

C1(C)C=CC(S(O)(=O)=O)=CC=1.[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH:19](O)[CH2:20][CH3:21].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH:19](/[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[Br:12])=[CH:20]\[CH3:21]

Komponenten

Versuchsvorschrift

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%).