Nitric Acid → HCID 71008792, compound

Participants

Reaction Conditions

Reaction Steps

Sulfuric acid (157 g, 85.2 ml, 1.6 mol) was cooled to −20° C. and 1-(2-fluoro-4-methoxyphenyl)ethanone (25 g, 149 mmol) was added portionwise in a manner that the temperature was kept below −15° C. Thereafter, a solution of sulfuric acid (64.4 g, 35 ml, 657 mmol) and fumic nitric acid (18.7 g, 12.4 ml, 297 mmol) was added dropwise within 20 minutes keeping the temperature below −15° C. After completion of the addition the viscous reaction mixture was stirred for additional 20 minutes at −15° C. For the workup, the reaction mixture was poured into a mixture of ice and water (400 ml) and stirring was continued for 10 minutes. The off-white suspension was filtrated and washed several times with water. The light yellow solid was dried at 45° C. before it was crystallized from a mixture of ethyl acetate and heptane (200 ml-600 ml, addition of charcoal). The 1-(2-fluoro-4-methoxy-5-nitro-phenyl)-ethanone (26.1 g, 82% yield) was obtained as pale yellow crystals. MS (ISP): m/z=214.2 [M+H]+. In addition, the regioisomer 1-(2-fluoro-4-methoxy-3-nitro-phenyl)-ethanone (0.6 g, 2% yield) was obtained as a white solid.

Provenance & Evidence