4-Iodophenol → HCID 18329731, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-iodophenol (20 g), 2-bromoethylmethyl ether (11.4 g), potassium carbonate (12.5 g) and dimethylformamide (100 ml) was stirred at 80° C. for 4 hours. A further portion of 2-bromoethylmethyl ether (2.24 g) and potassium carbonate (2.5 g) was then added and the mixture stirred at 80° C. for a further 1 hour. The dimethylformamide was removed by evaporation. The residue was treated with a 2M aqueous sodium hydroxide solution (50 ml) and the mixture extracted with diethyl ether (3×50 ml). The ethereal extracts were combined, washed with 2M aqueous sodium hydroxide solution (2×20 ml), brine (20 ml), dried (MgSO4) and evaporated to give 4-(2-methoxyethoxy)iodobenzene (23 g) as a white solid, m.p. 36-37° C. NMR ([CD3 ]2SO): 3.3 (3H, s), 3.6-3.7 (2H, m), 4.0-4.1 (2H, m), 6.72-6.82 (2H, d) and 7.52-7.62 (2H, d).

Provenance & Evidence