Nitrogen → 3-(Methylthio)-2-phenylthiophene

Participants

Reaction Conditions

Reaction Steps

Degas a solution of 2-iodo-3-methylsulfanyl-thiophene (18 g, 70.3 mmol), 4-bromobenzeneboronic acid (14.1 g, 70.3 mmol), potassium carbonate (21.4 g, 155 mmol), tetrakis(triphenylphosphine)-palladium (0) (8.1 g, 7.02 mmol) in a mixture of anhydrous dimethoxyethane (300 ml) and absolute ethanol (150 ml) with Ar or N2 for 15 min and stir for 12 hours at 80° C. Cool the reaction mixture to room temperature, add water (100 ml) and extract the crude product with dichloromethane (3×150 ml). Purify the title compound by column chromatography using hexane as eluent solvent yielding the title compound 12 g (60%) as a white solid.

Provenance & Evidence