Phenol, 4-bromo-, 1-acetate → Triacetylresveratrol

Participants

Reaction Conditions

Reaction Steps

A flask equipped with magnetic stirrer was charged with 50 mg (0.23 mmol, 1 eq) of 3,5-diacetoxystyrene, 49 mg (0.23 mmol) of 4-acetoxybromobenzene, 46 mg (0.27 mmol) of NaHCO3 and 78 mg (0.54 mmol, 2.4 eq) of tetrabutylammoniumchloride. The reactants were suspended in 2 ml DMF and the mixture was flushed with argon and then evacuated. The argon flushing and evacuation procedure was carried out three times. The reaction was started by adding 0.76 mg of palladium acetate in 50 μl of de-aerated DMF (3 μmol, 1.5 mol %), and stirred at 100° C. for three hours. Work-up of the reaction mixture following the procedure of Example 5 gave (E)-3,4′,5-triacetoxystilbene.

Provenance & Evidence