Toluene → 2-[4-(Pyrrolidin-1-yl)phenyl]acetic acid

Participants

Reaction Conditions

Reaction Steps

Toluene (10 ml) was added to a mixture of palladium acetate (22.3 mg, 0.10 mmol), 2-(biphenyl)-di-tert-butylphosphine (59.8 mg, 0.20 mmol) and sodium tert-butoxide (2.40 g, 25.0 mmol), and then (4-bromophenyl)acetic acid (2.15 g, 10.0 mmol) and pyrrolidine (1.10 ml, 13.2 mmol) were added thereto. The obtained mixture was heated at 70° C. for 46 hours. Water (20 ml) was added to the reaction mixture. pH of the aqueous layer was controlled at 2 or below. The aqueous layer was washed with toluene and adjusted to pH 4 to 5. After stirring the reaction mixture in ice-bath for a while, it was filtered to obtain the title compound in the form of a light yellow solid (1.1 g, 54%).

Provenance & Evidence