Trifluoromethanesulfonic anhydride → 3-Trifluoromethanesulfonyloxy-5-phenyltoluene

HRID 2228016Notes

Reaction equation

HRID 2228016 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].[CH3:16][C:17]1[CH:18]=[C:19](O)[CH:20]=[C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:22]=1>N1C=CC=CC=1>[F:5][C:4]([F:7])([F:6])[S:1]([O:8][C:19]1[CH:18]=[C:17]([CH3:16])[CH:22]=[C:21]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:20]=1)(=[O:3])=[O:2]

Participants

4

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 125778453-Methyl-5-phenylphenol

Product 1

HCID 184745743-Trifluoromethanesulfonyloxy-5-phenyltolueneYield 83%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Triflic anhydride (26 ml; 0.15 mol) was added to a solution of 3-methyl-5-phenylphenol (22.4 g; 0.15 mol) in pyridine (140 ml), at 0° C. The mixture was stirred at ambient temperature for 4 hours. After evaporation of the pyridine, the residue was acidified to pH 3 with 6N HCl and extracted with ether. The organic phase was evaporated and the residue purified by flash chromatography eluting with petroleum ether/ethyl acetate (94/6) to give 3-trifluoromethanesulfonyloxy-5-phenyltoluene as an oil. Yield=83%.

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 petroleum ether/ethyl acetate (94/6)

Sources & evidence

ORD record
ord-51e2d42035a749dbaafec5334c98e24c
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

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