p-Toluenesulfonic acid → HCID 18979058, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-fluoro 2-methoxyaniline (5.0 g) in 1,2-dichlorobenzene (50 ml) was heated to 170° C. and treated with p-toluenesulphonic acid (0.7 g). A solution of acrolein (4.0 g) in 1,2-dichlorobenzeue (20 ml) was added dropwise over 20 minutes. The reaction was stirred for 1 hour at 170° C. before being allowed to cool. The mixture was extracted with 2N hydrochloric acid (3×200 ml) and the combined extracts washed with dichloromethane (20 ml), basified with 25% aqueous sodium hydroxide, and extracted with ethyl acetate (3×200 ml). The combined extracts were dried over magnesium sulphate, filtered and the filtrate evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with 50% ethyl acetate in hexane to yield the desired product (2.6 g) as a clear oil.

Provenance & Evidence