Trifluoromethanesulfonic anhydride → Methyl 2-trifluoromethylsulfonyloxy-4-methylbenzoate

HRID 2228006Notes

Reaction equation

HRID 2228006 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 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 chromatography
  5. washeluting with a gradient of 0-5% ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-cf7a0885c1cd4a0ba636aead7fd32016
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

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