Trifluoromethanesulfonic anhydride → 4-(Trifluoromethyl)phenyl trifluoromethanesulfonate

HRID 1708066Notes

Reaction equation

HRID 1708066 reaction equation
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[F:16][C:17]([F:26])([F:25])[C:18]1[CH:23]=[CH:22][C:21](O)=[CH:20][CH:19]=1>ClCCl.N1C=CC=CC=1>[F:13][C:10]([F:11])([F:12])[S:7]([O:6][C:21]1[CH:22]=[CH:23][C:18]([C:17]([F:26])([F:25])[F:16])=[CH:19][CH:20]=1)(=[O:8])=[O:9]

Participants

5

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 678744-(Trifluoromethyl)phenol

Product 1

HCID 105656984-(Trifluoromethyl)phenyl trifluoromethanesulfonateYield 78.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent3×

Procedure

A solution of trifluoromethanesulphonic anhydride (1.0 g) in dichloromethane (2 ml) was added dropwise to a solution of 4-(trifluoromethyl)phenol (0.5 g) in dichloromethane (10 ml) and pyridine (0.5 ml) at 0° under nitrogen. The resulting suspension was stirred for 1 h at room temperature, diluted with dichloromethane (20 ml) and washed with aqueous sodium carbonate (2N; 20 ml). The dried organic phase was evaporated and the residue was purified by FCC eluting with ether to give the title compound as a colourless oil (710 mg).

Workup

  1. washwashed with aqueous sodium carbonate (2N; 20 ml)
  2. customThe dried organic phase was evaporated
  3. customthe residue was purified by FCC
  4. washeluting with ether

Sources & evidence

ORD record
ord-107154464e7a4eca9ec3b5366f01f148
Source dataset
uspto-grants-1994_10
Patent number
US05356893

Reaction notes

Loading…