Sodium Iodide → 2-[(4-Iodophenoxy)methyl]-2-methyloxirane

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-iodophenol (2.00 g, 9.09 mmol), powdered K2CO3 (2.54 g, 18.4 mmol), NaI (364 mg, 2.43 mmol) and 2-(chloromethyl)-2-methyloxirane (97) (0.90 mL, 9.31 mmol) in anhydrous DMF (5 mL) was stirred in a sealed vial at 70° C. for 15 h. Further 2-(chloromethyl)-2-methyloxirane (97) (0.18 mL, 1.86 mmol) was added and the mixture was then stirred at 73° C. for 17 h. The cooled mixture was added to ice/aqueous NaHCO3 (100 mL) and extracted with Et2O (5×100 mL). The extracts were washed with water (100 mL) and then evaporated to dryness and the residue was chromatographed on silica gel. Elution with 0-15% CH2Cl2/petroleum ether firstly gave foreruns, and then further elution with 15-20% CH2Cl2/petroleum ether gave 2-[(4-iodophenoxy)methyl]-2-methyloxirane (96) (1.81 g, 69%) as a white solid: mp (CH2Cl2/pentane) 40-41° C.; 1H NMR (CDCl3) δ 7.55 (dt, J=9.0, 2.7 Hz, 2H), 6.70 (dt, J=9.0, 2.7 Hz, 2H), 4.01 (d, J=10.5 Hz, 1H), 3.90 (d, J=10.5 Hz, 1H), 2.85 (d, J=4.7 Hz, 1H), 2.72 (d, J=4.7 Hz, 1H), 1.47 (s, 3H). Anal. (C10H11IO2) C, H, N.

Provenance & Evidence