Methane, dichloromethoxy- → 4-Chloro-5-ethyl-2-fluorobenzaldehyde

Participants

Reaction Steps

TiCl4 (0.90 mL) was added to 2-chloro-1-ethyl-4-fluorobenzene (645 mg, 4.1 mmol) at 0° C. and stirred to 10 min. Dichloro(methoxy)methane (0.725 mL) was added and the mixture was stirred overnight at ambient temperature. The mixture was diluted with CH2Cl2 (50 mL) and poured onto crushed ice (40 g). After stirring 30 min the layers were separated. The organic layer was washed with H2O (2×), brine (2×), dried (Na2SO4) and concentrated. Purification by flash chromatography (hexanes, EtOAc) yielded 440 mg of intermediate 390.2 as a light brown oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.18 (t, J=7.58 Hz, 3H) 2.69 (q, J=7.58 Hz, 2H) 7.05-7.29 (m, 1H) 7.67 (m, 1H) 10.23 (s, 1H).

Provenance & Evidence