Anisole → HCID 16107467, compound

Participants

Reaction Steps

To a stirred mixture of compound 8 (33.1 g, 48.0 mmol) and anisole (20.7 g, 192.0 mmol) in dichloromethane (200 mL) at 0° C. was slowly added powdered aluminum chloride anhydrous (19.5 g, 144.0 mmol). After the addition, the reaction mixture was allowed to warm to room temperature and stirred for additional 30 minutes. The reaction mixture was quenched by slowly addition of 1N HCl (100 mL) and the resulted mixture was extracted with ether (100 mL, 3 times). The combined organic layer was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (n-hexane/ethyl acetate=8/1) to give compound 9 as a clear oil (27.4 g, 99%). 1H NMR (400 MHz, CD3OD) δ 3.63 (s, 4H), 4.14 (s, 4H); 19F NMR (376 MHz, CD3OD) δ −71.14 (s); 13C NMR (100.7 MHz, CD3OD) δ 47.8, 60.4, 69.1, 80.9 (m), 121.8 (q, J=292.6 Hz); MS (CI) m/z 573 (M++1, 100); HRMS (CI) Calcd for C13H11F18O4: 573.0374, Found: 573.0374.

Provenance & Evidence