Potassium Phosphate, Tribasic → Ethyl 2-(3-bromo-5-phenylthiophen-2-yl)-2-(tert-butoxy)acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 2-(tert-butoxy)-2-(3,5-dibromothiophen-2-yl)acetate (10c) (70 mg, 0.17 mmol) in tetrahydrofuran (1 mL) were added tripotassium phosphate (111 mg, 0.52 mmol), phenylboronic acid (23 mg, 0.19 mmol) and a solution of palladium acetate (1.2 mg, 5.2 μmol) and xantphos (3.0 mg, 5.2 μmol) in tetrahydrofuran (1 mL) previously stirred for 5 minutes. The reaction mixture was heated at 60° C. for 3 hours. The mixture was then filtered and the precipitate was rinsed with dichloromethane (5 mL). The filtrate was concentrated in vacuo. The residue was purified by flash chromatography (cyclohexane/ethyl acetate 80/20) to provide the desired product (10d) (45 mg, 0.11 mmol, 65%).

Provenance & Evidence