Ammonia → Triphenylsulfonium 4-trifluoromethylbenzenesulfonate

HRID 2057142Notes

Reaction equation

HRID 2057142 reaction equation
[Br-].[C:2]1([S+:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])OCC.[F:27][C:28]([F:40])([F:39])[C:29]1[CH:34]=[CH:33][C:32]([S:35]([OH:38])(=[O:37])=[O:36])=[CH:31][CH:30]=1.N>C(Cl)Cl>[F:40][C:28]([F:27])([F:39])[C:29]1[CH:30]=[CH:31][C:32]([S:35]([O-:38])(=[O:36])=[O:37])=[CH:33][CH:34]=1.[C:15]1([S+:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 98779144-(Trifluoromethyl)benzene-1-sulfonic acidHCID 11984010Triphenylsulfonium BromideHCID 53630039Ethylorthoformate

Product 1

HCID 22057398Triphenylsulfonium 4-trifluoromethylbenzenesulfonateYield 76.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphenylsulfonium bromide (343 mg; 1 mmol), ethyl orthoformate (296 mg; 2 mmol), and 4-trifluoromethylbenzenesulfonic acid (271 mg; 1.2 mmol) were dissolved in methylene chloride (10 ml), and the mixture was stirred for 6 hours at room temperature. The reaction mixture was alkalinized by adding 1% aqueous ammonia (10 ml), and subjected to extraction with methylene chloride three times, followed by drying. The solvent was removed through distillation, to thereby yield solid matter. The solid matter was washed and stirred in ether, to thereby yield 375 mg of the target compound as white crystals (yield: 76%).

Workup

  1. extractionsubjected to extraction with methylene chloride three times
  2. customby drying
  3. customThe solvent was removed through distillation
  4. customto thereby yield solid matter
  5. washThe solid matter was washed
  6. stirringstirred in ether

Sources & evidence

ORD record
ord-b47ee0c063ed42ed80c67645649fcacf
Source dataset
uspto-grants-2008_02
Patent number
US07335787B2

Reaction notes

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