Acetic Acid → HCID 10858478, compound

Participants

Reaction Conditions

Reaction Steps

To a 1-L three-necked flask equipped with an overhead stirrer, thermometer, and vented addition funnel was charged 71.8 g (0.304 mol) of 4-[(difluoromethyl)thio]-1,1'-biphenyl, 280 mL of glacial acetic acid, and 3.0 g of sodium tungstate predissolved in 10 mL of water. The mixture was heated to 60° C., heating was removed, and 90 mL (0.87 mol, 2.9 equiv) of 30% hydrogen peroxide was added dropwise, maintaining the temperature at 60-70° C. After the addition was complete, the mixture was heated at 80° C. for 2 h to finish the conversion. The solution was cooled to 25° C. and 140 mL of water was added gradually to complete precipitation of the product. The product was filtered, washed with three 50-mL portions of water, suction-dried, then washed with 150 mL of isopropanol, suction-dried, and oven-dried at 50° C./150 mm to afford 78 g (96%) of ca. 98%-pure 4-[(difluoromethyl)sulfonyl]-1,1'-biphenyl, m.p. 81-83° C. An analytical sample prepared by recrystallization from isopropanol/water had m.p. 83-85° C. IR(KBr): 1593, 1334, 1159, 1113, 1080, 754, 607 cm-1. 1H-NMR(CDCl3): δ6.22 (t, 1H, J=60 Hz), 7.5 (m, 3H), 7.62 (dd, 2H, 7.82 (d, 2H), 8.05 (d, 2H). 13C-NMR (CDCl3): δ114.7 (t, JCF =286 Hz), 127.4, 128.1, 129.1, 129.2, 130.1, 131.1, 138.6, 148.8 ppm. 19F-NMR (CDCl3): δ-120.5 (d, JHF =53.4 Hz).

Provenance & Evidence