Trifluoroacetic acid → 1-(2-Fluoro-3-hydroxy-6-nitrophenyl)propan-2-one

Participants

Reaction Steps

To a solution of tert-butyl 2-(2-fluoro-3-hydroxy-6-nitrophenyl)-3-oxobutanoate (7.89 g) in dichloromethane was added trifluoroacetic acid (11.2 g) and the mixture stirred at ambient temperature for 20 hours. The mixture was concentrated to a thick paste and toluene (14 ml) added and the mixture distilled on a rotary evaporator (77 mbar, bath 40° C.). Further toluene (14 ml) was added and the mixture distilled. Sodium hydroxide (7.4% w/w, 20 ml) was added and the lower aqueous layer separated and washed with toluene (18 ml). The aqueous layer was diluted with water (20 ml) and warmed to 40° C. Acetic acid (13 ml) was added followed by sulphuric acid (20% w/w, 20 ml). The mixture was cooled to 0° C. and further water (43 ml) added. The mixture was cooled to −5° C. and left overnight. The solid was filtered and washed with water (24 ml). The solid was dried in a vacuum oven to give 1-(2-fluoro-3-hydroxy-6-nitrophenyl)-propan-2-one (1.65 g, 30.7%).

Provenance & Evidence