Fluorobenzene → HCID 10669907, compound

HRID 323918Notes

Reaction equation

HRID 323918 reaction equation
[F:1][C:2]([S:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O)([F:4])[F:3].[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[O:20](S(C(F)(F)F)(=O)=O)[S:21]([C:24]([F:27])([F:26])[F:25])(=[O:23])=[O:22]>>[O-:23][S:21]([C:24]([F:27])([F:26])[F:25])(=[O:22])=[O:20].[F:3][C:2]([F:1])([F:4])[S+:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:17]1[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=1

Participants

4

Reactant 3

HCID 10008FluorobenzeneHCID 67749Trifluoromethanesulfonic anhydrideHCID 9794162PHENYL TRIFLUOROMETHYL SULFOXIDE

Product 1

HCID 10669907HCID 10669907, compound

Conditions

Temperature
0 °C

Procedure

Synthetic details: To a solution of phenyl trifluoromethyl sulfoxide (5) (582 mg, 3.0 mmol) in dry 1-fluorobenzene (8.4 mL, 30 mmol) was added (CF3SO2)2O (2.5 mL, 15 mmol) at 0° C. The reaction mixture was stirred for 10 h at 0° C., and then at rt for another 2 h. Removal of the solvent left a crude residue that was subjected to column chromatography on silica gel using CH3CN—CH2Cl2 (1:4) as eluent to give the product as white crystals (886 mg, 70%), mp 80-1 C (recrystallized from ethyl acetate/hexanes). IR (nujol): 3108 (m), 1719 (w), 1589 (m), 1494 (m), 1255 (s), 1171 (s), 640 (s) cm−1; 1H NMR (CDCl3): 8.35 (dd, J23=6.0 Hz, J2F=4.0 Hz, 2H), 8.19 (bd, J2′3′=6.0 Hz, 2H), 7.83 (m, 3H), 7.51 (dd, J32=6.0 Hz, J3F=9.0 Hz, 2H); 19F NMR (CDCl3): −50.7 (s, 3F), −78.7 (s, 3F), −95.5 (s, 1F); 13C NMR (CDCl3): 170 (d, J=261 Hz), 139, 137, 135, 135, 127 (q, J=265 Hz), 126 (q, J=263 Hz), 121, 116 ppm; FAB+-MS [m/e (species, intensity)]: 273 ((Cl3H9F4S)+, 100), 272 ((C13H8F4S)+, 14.2), 254 ((C13H9F3S)+, 5.9), 204 ((C13H9F4S)+-CF3, 98.0), 196 ((C13H9F4S)+-C6H5, 5.3), 178 ((C13H9F4S)+-C6H4F, 3.4), 127 ((C6H4FS)+, 13.0), 109 ((C6H5S)+, 20.1) ); Chemical analysis: Calculated for C14H9F7O3S2: C, 39.81; H, 2.15. Found: C, 39.45; H, 2.17.

Workup

  1. waitat rt for another 2 h
  2. customRemoval of the solvent
  3. waitleft a crude residue that
  4. customto give
  5. customthe product as white crystals (886 mg, 70%), mp 80-1 C (recrystallized from ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-6a77ec8496db4e459356adefb8401f59
Source dataset
uspto-grants-2001_04
Patent number
US06215021B1

Reaction notes

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