Benzoyl Peroxide → 4-(4-Fluorobenzoyl)benzyl bromide

Participants

Reaction Steps

A mixture of 2.0 g (9.9 mmol) of 4-methyl-4′-fluorobenzophenone, 1.524 g (9.9 mmol) of recrystallized N-bromosuccinimide, 170 mg benzoyl peroxide, and 20 mL CCl4 was 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 reduced vacuum. The crude product was recrystallized from hexane and dried under vacuum. The resultant yield was 43%. Rf=0.25 (ethyl Acetate/hexane; 15:85). 1H-NMR: δ 7.85 (dd, aromatic, 2H), 7.75 (d, aromatic, 2H), 7.51 (d, aromatic, 2H), 7.17 (dd, aromatic, 2H), 4.52 (s, methyl, 3H). 13C-NMR: δ 195.0 (carbonyl); 166.5, 164.5, 142.5, 138.5, 133.4, 130.4, 129.2, 115.8, 115.5 (aromatic); 31.1 (alkyl).

Provenance & Evidence