Thionyl Chloride → 3-(Methylsulfonyl)-5-(trifluoromethyl)benzoyl chloride

HRID 403398Notes

Reaction equation

HRID 403398 reaction equation
ClC1N=NC(N(C)[C:9](=[O:24])[C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:11]=2)=C(C2C=CC(F)=CC=2OC)C=1.S(Cl)([Cl:37])=O>CN(C)C=O>[CH3:23][S:20]([C:12]1[CH:11]=[C:10]([CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=1)[C:9]([Cl:37])=[O:24])(=[O:22])=[O:21]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 71766083HCID 71766083, compound2×

Product 1

HCID 866708083-(Methylsulfonyl)-5-(trifluoromethyl)benzoyl chlorideYield 102.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

To 3-(methylsulfonyl)-5-(trifluoromethyl)benzoic acid (1 g, 3.73 mmol, example 1, intermediate d) was added N,N-dimethylformamide (27.3 mg, 28.9 μL, 373 μmol) and thionyl chloride (8.87 g, 5.44 ml, 74.5 mmol) and the suspension was heated to reflux for 30 min. A light brown solution was formed. To remove thionyl chloride, the light brown solid was diluted with toluene, followed by complete evaporation. This procedure was repeated two times to provide the desired compound as a colorless solid (1.1 g; 99%) which was pure enough for the next step without further purification.

Workup

  1. temperaturethe suspension was heated
  2. temperatureto reflux for 30 min
  3. customA light brown solution was formed
  4. customTo remove thionyl chloride
  5. additionthe light brown solid was diluted with toluene
  6. customfollowed by complete evaporation

Sources & evidence

ORD record
ord-14b60bfe2f4b41238fc2159eb0034bb1
Source dataset
uspto-grants-2014_06
Patent number
US08748434B2

Reaction notes

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