Acetic Anhydride → HCID 70974575, compound

Participants

Reaction Steps

Into the solution of 4-((Perfluoropyridin-4-yl)ethynyl)aniline, (13a) (0.158 g, 0.59 mmol) in 3 mL of CH2Cl2 were added acetic anhydride (0.134 g, 1.26 mmol) and Et3N (0.128 g, 1.26 mmol). The reaction mixture was stirred at room temperature overnight. After concentrating the solution in vacuo, the product was isolated by column chromatography (EtOAc:Hexane=1:2 to 1:1) with 85% yield: 1H-NMR (400 MHz, CD3OD) δ 7.70 (d, J=8.6 Hz, 2H), 7.59 (d, J=8.6 Hz, 2H), 2.15 (s, 3H); 13C-NMR (150 MHz, CD3CN) δ 170.1, 144.5 (dm, J=237 Hz), 143.1 (dm, J=259 Hz), 142.7, 134.2, 120.0, 115.4, 107.5 (t, J=3.4 Hz), 73.6 (t, J=4.3 Hz), 24.5; HRMS (ESI+): calcd for C15H9F4N2O1 [M+H]+ 309.06510, found 309.06678; m.p. 189-190° C.

Provenance & Evidence