4-Bromotoluene → 2-(4-Methylphenyl)thiophene

Participants

Reaction Steps

The corresponding Grignard compound is prepared from 16 g of 4-bromotoluene and 2.23 g of magnesium in 150 ml of THF. This is added dropwise at room temperature to a solution of 10 g of 2-bromothiophene, 3 g of palladium acetate and 1.27 g of triphenylphosphine in 150 ml of THF. The mixture is boiled at reflux under argon for 3.5 hrs., then poured on to ice-water and extracted with ethyl acetate. Chromatography on silica gel (toluene) gives 9.06 g of 2-p-tolyl-thiophene.

Provenance & Evidence