Thionyl Chloride → HCID 21942520, compound

Participants

Reaction Steps

A solution of Example 59B (535 mg, 3.24 mmol) in thionyl chloride (3855 mg, 32.4 mmol) was heated at 90° C. for 2 hours. The solution was cooled, concentrated, diluted with toluene, and concentrated to afford 2-fluoro-5-cyanobenzoyl chloride which was used without purification. The title compound was prepared and isolated as described in Example 22B, substituting 2-fluoro-5-cyanobenzoyl chloride for 2-fluoro-5-(trifluoromethyl)benzoyl chloride, in 61% yield. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.33 (s, 9 H) 1.58-1.72 (m, 1H) 1.82 (qd, J=7.01, 6.74 Hz, 2 H) 1.90-1.97 (m, 1 H) 3.61-3.70 (m, 1 H) 3.74-3.83 (m, 1H) 4.24-4.35 (m, 3 H) 7.33 (s, 1 H) 7.52 (dd, J=10.71, 8.72 Hz, 1 H) 8.02-8.07 (m, 1 H) 8.40 (dd, J=6.94, 2.18 Hz, 1 H); MS (DCI/NH3) m/z 388 (M+H)+.

Provenance & Evidence