4-Fluorobenzoyl chloride → HCID 18931034, compound

Participants

Reaction Steps

To a stirred suspension of 4-fluorobenzoyl chloride (2.89 mL, 24.5 mmol), bis(triphenylphosphine)palladium (II) chloride (1.08 g, 1.54 mmol) and zinc dust (3.20 g, 49 mmol) in anhydrous dimethoxyethane (50 mL) was added a solution of the title compound of Step B (5.06 g, 24.5 mmol) in dimethoxyethane (50 mL) at room temperature under N2 over 45 min. After 20 h, the suspension was filtered through Celite® washed with ethyl acetate. The filtrate was washed with water and saturated aqueous NaCl, dried over MgSO4, and concentrated in vacuo to a yellow solid. Purification by flash chromatography eluting with 17-60% ethyl acetate/hexanes afforded the title compound of Step C as a yellow solid (0.77 g) which was somewhat impure by 1H NMR. 1H NMR (CDCl3, 300 MHz) δ8.30 (dd, 1H), 8.10 (m,2H), 7.6 (dd, 1H), 7.0-7.4 (m,3H), 4.40 (s,2H).

Provenance & Evidence