Chloromethyl Methyl Ether → HCID 59540873, compound

Participants

Reaction Steps

A solution of 3-amino-5-bromo-phenol (3.0 g, 15.96 mmol) in dry DMF (35 ml) was cooled (ice bath) under nitrogen. Sodium hydride (732 g, 18.36 mmol, 60% in oil) was added in 2 equal portions over 5 minutes. After 10 minutes stirring the material was warmed to ambient. Chloromethylmethyl ether (1.38 ml, 18.4 mmol) was added slowly, via syringe. The material was stirred for 2 hours. The solvent was stripped (rotovap/pump) providing a crude remainder which was treated with a solution of saturated aqueous NH4Cl (25 ml), water (35 ml) and ethyl acetate (60 ml). The material was shaken in a reparatory funnel and the organic phase was collected and washed with an equal volume of brine. The aqueous phases were back extracted with ethyl acetate (2×50 ml) and the organics combined, dried (MgSO4), filtered and stripped to provide a viscous oil. The crude was purified by silica gel chromatography using 4%-30% EtOAc in hexanes as eluant to provide 3.50 g of 3-bromo-5-methoxymethoxy-phenylamine as a light yellow mobile oil.

Provenance & Evidence