Sodium hydride → HCID 68828889, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 4-bromo-3-hydroxybenzoate (143 mg) and 4-(2-iodoethyl)morpholine.HCI (189 mg) were combined in DMF (10 ml). Sodium hydride (55 mg, 60% dispersion in mineral oil) was added and the reaction heated at 80° C. under nitrogen for 5 hours. The reaction was quenched with water (10 ml) and the solvent evaporated under vacuum. Ethyl acetate/chloroform (1:1, 30 ml) and water (30 ml) were added to the residue resulting in precipitation of a solid, which was filtered off and washed with ether. The solid was partitioned between ethyl acetate/chloroform (1:1, 2×50 ml) and aqueous sodium hydrogen carbonate solution (1 M, 50 ml). The organic layers were combined, dried over a hydrophobic filter and evaporated to give methyl 4-bromo-3-{[2-(4-morpholinyl)ethyl]oxy}benzoate as a yellow gel (103 mg).

Provenance & Evidence