Benzoyl Peroxide → HCID 58969780, compound

Participants

Reaction Steps

A mixture of 233 mg (1 mmol) of 4-methyl-2′,6′-difluorobenzophenone, 178 mg (1 mmol) of recrystallized N-bromosuccinimide, 17 mg benzoyl peroxide, and 3 mL CCl4 were refluxed under argon for 3 hours. The hot solution was filtered through a glass sintered filter and rinsed with 20 mL of hot CCl4 until the crystals became colorless. The crystals were washed with 6 mL of cold CCl4 and the solution was concentrated under vacuum. The crude product was purified by column chromatography on a silica gel flash column (13 cm×55 mm) eluted with ethyl acetate/hexane (15:85) and then concentrated under vacuum. The product was allowed to dry under high vacuum overnight. The resultant yield was 55%. Rf=0.3 (ethyl Acetate/hexane; 15:85). 1H-NMR: δ 7.84 (d, 2H, aromatic), 7.50 (d, 2H, aromatic), 7.46 (t, 1H, aromatic), 7.01 (m, 2H, aromatic), 4.51 (s, 2H). 13C-NMR (CDCl3): δ 188.1 (carbonyl); 160.8, 158.8, 143.9, 136.6, 132.0, 130.0, 129.4, 111.9 (aromatic), 31.8 (alkyl bromide).

Provenance & Evidence