4-Bromotoluene → 3-(4-Methylphenyl)thiophene

Participants

Reaction Steps

A solution of 4-bromotoluene (0.9 ml, 7.3 mmol) in THF (3 ml) is added to dried magnesium turnings (0.815 g, 33.5 atoms) under nitrogen atmosphere. After the exothermic reaction initiates, a solution of 4-bromotoluene (3.16 ml, 25.7 mmol) in THF (3 ml) is dropped to the reaction mixture. The stirring is continued for 10 min. The mixture is dropped to a suspension of 3-bromothiophene (2.8 ml, 29.9 mmol) and [1,2-bis(diphenylphosphino)-ethane]nickel(II) chloride (0.72 g, 1.4 mmol) in diethyl ether (50 ml), which has been stirred for 10 min. The reaction mixture is cooled and quenched with 1N hydrochloric acid and extracted with ether. The organic layer is washed with saturated sodium bicarbonate and brine, dried over magnesium sulfate and concentrated in vacuo. The residue is recrystallized from ethanol to give 4-(3-thienyl)toluene.

Provenance & Evidence