Methanesulfonyl chloride → N-[2-bromo-5-(trifluoromethyl)phenyl]methanesulfonamide

HRID 505671

Reaction equation

HRID 505671 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:3]=1[NH2:4].[CH3:13][S:14](Cl)(=[O:16])=[O:15]>N1C=CC=CC=1>[Br:1][C:2]1[CH:8]=[CH:7][C:6]([C:9]([F:10])([F:11])[F:12])=[CH:5][C:3]=1[NH:4][S:14]([CH3:13])(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 679892-Bromo-5-(trifluoromethyl)benzenamine

Product 1

HCID 59430904N-[2-bromo-5-(trifluoromethyl)phenyl]methanesulfonamideYield 52%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-bromo-5-trifluoromethylaniline (3.18 g, 13.25 mmol) in pyridine (18 ml) was added methanesulfonyl chloride (1.03 ml, 13.25 mmol) and the mixture was stirred for 6 hours at room temperature. The solvent was removed in vacuo and the residue was diluted with chloroform. The organic layer was washed with water, 1N hydrochloric acid, a saturated sodium hydrogen carbonate solution and saturated brine and dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified by recrystallization to give the subject compound (2.18 g, 52%).

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was diluted with chloroform
  3. washThe organic layer was washed with water, 1N hydrochloric acid
  4. dry with materiala saturated sodium hydrogen carbonate solution and saturated brine and dried over anhydrous sodium sulfate
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by recrystallization

Sources & evidence

ORD record
ord-5888ddb31d474185be9e29694440c5d9
Source dataset
uspto-grants-2010_08
Patent number
US07781479B2

Linked notes

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