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

Participants

Reaction Conditions

Reaction Steps

To a suspension of methyl 3-methyl-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (4.5 g, 10.63 mmol) in carbon tetrachloride (53.1 mL) was added N-bromosuccinimide (2.459 g, 13.82 mmol) and benzoyl peroxide (0.257 g, 1.063 mmol). The mixture was heated at 100° C. for 20 h, Additional portions of N-bromosuccinimide (0.3 equiv., 0.568 g, 3.19 mmol) and benzoyl peroxide (0.257 g, 1.063 mmol) were added, and the reaction mixture was heated at 100° C. for 5 h longer. The mixture was cooled to room temperature and concentrated in vacuo to give methyl 3-(bromomethyl)-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate. This material was used in the next step without further purification. MS (m/z) 503.9 (M+H+).

Provenance & Evidence