Trichloroacetyl chloride → HCID 86750013, compound

HRID 1901303Notes

Reaction equation

HRID 1901303 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.[O-][O-].[Na+].[Na+].ClC(Cl)(Cl)C(Cl)=[O:35]>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:35]

Participants

5

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 14803Sodium peroxideHCID 23133109HCID 23133109, compound

Product 1

HCID 86750013HCID 86750013, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

(Tolyl)diphenylsulphonium hexafluorophosphate (1.08 g, 2.57 mol) is dissolved in methanol (40 ml) with cooling in an ice-water bath. Sodium peroxide (2.42 g, 31 mmol) is added slowly. After 15 mins a solution of trichloro- acetyl chloride (1.4 ml, 12.5 mol) in methanol (30 ml) is added over 20 mins. After a further 30 mins the reaction mixture is filtered under vacuum and the filtrate evaporated in vacuo. Water is added and the resulting solid collected, washed with water and ether to give (tolyl)diphenylsulphoxonium hexafluorophosphate (0.72 g, 64% ) with spectra identical to those of authentic material.

Workup

  1. temperaturewith cooling in an ice-water bath
  2. filtrationAfter a further 30 mins the reaction mixture is filtered under vacuum
  3. customthe filtrate evaporated in vacuo
  4. additionWater is added
  5. customthe resulting solid collected
  6. washwashed with water and ether

Sources & evidence

ORD record
ord-346efaeb2bc9431fa582245bbf596f57
Source dataset
uspto-grants-1996_11
Patent number
US05576461

Reaction notes

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