1-Ethynyl-4-pentylbenzene → 2,5-Dibromo-3-(4-pentylphenyl)ethynylthiophene

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,5-dibromo-3-iodothiophene (3.52 grams, 9.57 mmol) and 1-ethynyl-4-pentylbenzene (1.65 grams, 9.57 mmol) in triethylamine (50 milliliters) were added dichlorobis(triphenylphosphine)palladium (II) (0.28 gram, 0.4 mmol) and copper(I) iodide (38 milligrams, 0.2 mmol) at 0° C. under argon. The resulting reaction mixture was stirred at 0° C. for 6 hours and at room temperature for 20 hours under argon. After evaporation of the solvent, the product obtained was purified by column chromatography on a silica gel using hexane as eluent. 2,5-Dibromo-3-(4-pentylphenyl)ethynylthiophene was obtained as a colorless liquid was. Yield: 3 grams (73 percent).

Provenance & Evidence