Benzoyl Peroxide → Methyl 3-(bromomethyl)-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 3-methyl-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (2 g, 4.72 mmol), benzoyl peroxide (0.114 g, 0.472 mmol) and NBS (1.093 g, 6.14 mmol) was suspended in carbon tetrachloride (31.5 mL) and heated to reflux for 4 h. Additional benzoyl peroxide (0.571 g, 2.36 mmol) was added, and the mixture was stirred at 100° C. for 24 h. Additional benzoyl peroxide (0.571 g, 2.36 mmol) was added, and the mixture stirred for 3 h. Additional benzoyl peroxide (0.571 g, 2.36 mmol) and NBS (0.250 g, 1.42 mmol) were added, and the mixture was heated for 2.5 h. The mixture was cooled to room temperature, and the solvent was removed under reduced pressure to afford methyl 3-(bromomethyl)-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate. This material was used without further purification. MS (m/z) 502.0 (M+H+).

Provenance & Evidence