Trifluoromethanesulfonic anhydride → Methyl 2-trifluoromethylsulfonyloxy-4-methylbenzoate

HRID 1251863Notes

Reaction equation

HRID 1251863 reaction equation
[S:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2].O[C:17]1[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:18]=1[C:19]([O:21][CH3:22])=[O:20]>N1C=CC=CC=1>[F:5][C:4]([F:7])([F:6])[S:1]([O:8][C:17]1[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:18]=1[C:19]([O:21][CH3:22])=[O:20])(=[O:3])=[O:2]

Participants

4

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 78400Benzoic acid, 2-hydroxy-4-methyl-, methyl ester

Product 1

HCID 18474576Methyl 2-trifluoromethylsulfonyloxy-4-methylbenzoateYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Triflic anhydride (170 ml; 1.01 mol) was added to a solution of methyl 2-hydroxy-4-methylbenzoate (153 g; 0.92 mol) in pyridine (1.5 l), at 0° C., The mixture was stirred at ambient temperature overnight. After evaporation of the pyridine, the residue was acidified to pH 3.5 with 6N HCl and extracted with ether. The organic phase was evaporated and the residue purified by flash column chromatography eluting with a gradient of 0-5% ethyl acetate/petroleum ether to give methyl 2-trifluoromethylsulfonyloxy-4-methylbenzoate (245 g; 90%).

Workup

  1. customAfter evaporation of the pyridine
  2. extractionextracted with ether
  3. customThe organic phase was evaporated
  4. customthe residue purified by flash column chromatography
  5. washeluting with a gradient of 0-5% ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-48e90b10d89b4e44a278b461139c376e
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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