Trifluoroacetic anhydride → HCID 86750013, compound

HRID 1901305Notes

Reaction equation

HRID 1901305 reaction equation
[F:1][P-:2]([F:7])([F:6])([F:5])([F:4])[F:3].[C:8]1([CH3:27])[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S+:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C[O-].[Na+].FC(F)(F)C(OC(=O)C(F)(F)F)=[O:34]>CO>[F:1][P-:2]([F:7])([F:6])([F:5])([F:4])[F:3].[C:8]1([CH3:27])[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S+:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:34]

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 10942334Sodium MethoxideHCID 23133109HCID 23133109, compound

Product 1

HCID 86750013HCID 86750013, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

(Tolyl)diphenylsulphonium hexafluorophosphate (1.08 g, 2.57 mol) is dissolved with stirring in methanol (40 ml) with cooling in an ice-water bath. Sodium methoxide (2.42 g, 31 mmol) is added slowly. After 15 mins a solution of trifluoroacetic anhydride (1.8 ml, 12.5 mmol) in methanol (30 ml) is added dropwise over 25 min. After 30 min the reaction mixture is filtered and evaporated under reduced pressure. Water is added and the resulting solid is collected and washed with water and ether, to give (tolyl)diphenylsulphoxonium hexafluorophosphate (0.85 g, 76%) identical to authentic material.

Workup

  1. temperaturewith cooling in an ice-water bath
  2. filtrationAfter 30 min the reaction mixture is filtered
  3. customevaporated under reduced pressure
  4. additionWater is added
  5. customthe resulting solid is collected
  6. washwashed with water and ether

Sources & evidence

ORD record
ord-4f2f7ac663a54e4eb4b7940accf08be8
Source dataset
uspto-grants-1996_11
Patent number
US05576461

Reaction notes

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