Dimethylformamide → 3-(Methylsulfonyl)-5-(trifluoromethyl)benzoyl chloride

HRID 878258Notes

Reaction equation

HRID 878258 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=1)[C:8](O)=[O:9])(=[O:4])=[O:3].CN(C=O)C.O=S(Cl)[Cl:25]>C1(C)C=CC=CC=1>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=1)[C:8]([Cl:25])=[O:9])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 215445163-Methanesulfonyl-5-(trifluoromethyl)benzoic acid

Product 1

HCID 866708083-(Methylsulfonyl)-5-(trifluoromethyl)benzoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-methanesulfonyl-5-trifluoromethyl-benzoic acid (70 mg, 0.26 mmol) in toluene (5 mL) were added catalytic amount of DMF and SOCl2 (0.2 mL, 2.61 mmol) and the reaction mixture was heated to reflux for 6 hours. The solvent was evaporated and the resulting 3-methanesulfonyl-5-trifluoromethyl-benzoyl chloride (70 mg, crude) was used in the next step without further purification.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 6 hours
  3. customThe solvent was evaporated
  4. customthe resulting 3-methanesulfonyl-5-trifluoromethyl-benzoyl chloride (70 mg, crude) was used in the next step without further purification

Sources & evidence

ORD record
ord-6d912ab957cf4e138ec29442bbf5762a
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

Loading…