Methane, dichloromethoxy- → 5-(1-Cyanocyclopropyl)-2-methoxybenzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of Compound 1 (2.0 g, 11.6 mmol) in dry CH2 Cl2 (50 ml) was added TiCl4 (5.7 ml, 52.0 mmol) with cooling (-10° C.). After 15 min., to this was added a solution of dichloromethyl methyl ether (2.0 g, 17.3 mmol) in dry CH2Cl2 (5 ml) dropwise. The reaction mixture was stirred at same temperature for 10 min. and then at room temperature for 1 h. The mixture was poured into ice-water and stirred at room temperature for 15 min. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined solution was washed with brine, dried (MgSO4) and concentrated in vacuo to give crude product (2.36 g) as a yellow solid. The crude product was recrystallized from hexane-ethyl acetate to give Compound 2 (2.04 g, 88%) as a yellow solid.

Provenance & Evidence