Chloromethyl Methyl Ether → HCID 59200370, compound

Participants

Reaction Conditions

Reaction Steps

To stirring solution of 2-iodobenzyl alcohol (6.02 g, 25.72 mmol) in dichloromethane (40 mL) was added sequentially Hunig's base (6.8 mL, 38.51 mmol) followed by MOMCl (3.0 mL, 39.13 mmol), and stirred at 23° C. overnight. The reaction was treated with saturated NH4Cl (30 mL), stirred vigorously for several minutes, then the phases separated. The organic phase was extracted with dichloromethane (2×). The combined organics were dried (MgSO4), filtered and concentrated to an amber oil which was purified on Biotage Horizon (10-100% (7:3 hexane:EtOAc)/hexane, 40+M, SiO2) to afford the product (6.06 g) as an oil: 1H NMR (400 MHz, CDCl3) δ ppm 7.83 (dd, J=7.83, 1.26 Hz, 1H), 7.45 (dd, J=7.70, 1.64 Hz, 1H), 7.35 (td, J=7.52, 1.14 Hz, 1H), 6.99 (td, J=7.58, 1.77 Hz, 1H), 4.76 (s, 2H), 4.59 (s, 2H), 3.43 (s, 3H).

Provenance & Evidence