3-Bromo-1,1,1-trifluoro-2-propanone → HCID 19047036, compound

Participants

Reaction Steps

The product from Step B (5.5 g, 0.028 mol) was dissolved in ethyl alcohol (100 mL). 3-bromo-1,1,1-trifluoroacetone (5.3 g, 0.028 mol) was added and the resulting solution refluxed for 3 h. After cooling to room temperature, the reaction mixture was evaporated to dryness. The residue was partitioned between ethyl acetate and 10% aqueous sodium carbonate (200 mL each). The organic layer was separated, dried (MgSO4) and then concentrated to give an oil. Flash chromatography of this oil on silica gel eluting with 20% ethyl acetate/hexane afforded a solid which was further purified by recrystallization from chlorobutane/hexane. Yield: 4.4 g (51%) of the title compound as a white solid melting at 148°-151° C. 1H NMR (300 MHz, CDCl3) δ 7.96-7.98 (m,1H), 7.42-7.44 (m,2H), 3.86-3.89 (m,1H), 3.34 (s,1H), 2.49 (s,3H).

Provenance & Evidence