Triphenylphosphine → Tert-butyl 2-(4-(5-(4-chlorophenyl)thiazol-2-yl)phenoxy)acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 2-(4-(thiazol-2-yl)phenoxy)acetate (360 mg, 1.23 mmol) and 1-chloro-4-iodobenzene (412.5 mg, 1.73 mmol) in anhydrous acetonitrile (ACN) (5.2 mL) was added PPh3 (32.74 mg, 124 μmol) and Ag2CO3 (685.2 mg, 2.46 mmol). The flask was evacuated and re-filled with nitrogen three times and then PdCl2dppf was added (50.5 mg, 0.062 mmol). The reaction mixture was heated under Ar atmosphere for 72 h at 60° C. When the reaction was completed, the reaction mixture was filtered through Celite® (inorganic solids were removed) and the precipitate was washed with several portions of dichloromethane(3×20 mL). The filtrate was evaporated, and the residue was absorbed onto silica then subjected to flash chromatography (SiO2, hexane: ethyl acetate (AcOEt), 9:1) to afford 322.5 mg of tert-butyl 2-(4-(5-(4-chlorophenyl)thiazol-2-yl)phenoxy)acetate as a yellow solid (76% yield). RMN1H (CDCl3, 400 MHz): δ 7.94; (s, 1H), 7.92-7.87; (m, 2H), 7.56-7.46; (m, 2H), 7.42-7.35; (m, 2H), 7.01-6.93; (m, 2H), 4.57; (d, J=3.6 Hz, 2H), 1.50; (s, 9H) ppm.

Provenance & Evidence