Hydrochloric Acid → 3-(2-Methylphenyl)thiophene

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-bromotoluene (11.7 mmol) in tetrahydrofuran (25 mL) at -78° C. under nitrogen was added n-butyllithium in hexane (11.7 mmol) and the resulting yellow suspension stirred for 45 minutes at -78° C. To this suspension at -78° C. was added magnesium bromide etherate (11.5 mmol) and after stirring for 15 minutes at -70° C., the reaction mixture was allowed to warm to ambient temperature over 45 minutes. The resultant solution was added at ambient temperature to a suspension of 3-bromothiophene (11.0 mmol) and bis(1,2-diphenylphosphino)ethane nickel (II) chloride (0.05 mmol) in diethyl ether (25 mL) that has been stirred for 15 minutes. The reaction mixture was heated at reflux for 16 hours and then cooled in an ice bath. To the cooled reaction mixture was added dilute hydrochloric acid (20 mL) and then diethyl ether (50 mL). The organic phase was washed with saturated aqueous sodium bicarbonate, brine and dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue fractionated to give Compound 2a as a clear oil (b.p. 110°-114° C./7 mm).

Provenance & Evidence