Methanesulfonyl chloride → N-(4-bromo-2-fluorophenyl)methanesulfonamide

HRID 1677150Notes

Reaction equation

HRID 1677150 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.[CH3:10][S:11](Cl)(=[O:13])=[O:12]>ClCCl.N1C=CC=CC=1>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][S:11]([CH3:10])(=[O:13])=[O:12])=[C:4]([F:9])[CH:3]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 1230504-Bromo-2-fluoroaniline

Product 1

HCID 956286N-(4-bromo-2-fluorophenyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 21875418Pyridine methylene chlorideSolvent

Procedure

Procedure MM: To a stirring solution of 4-bromo-2-fluoroaniline (1.0 mmol) in 3:1 dichloromethane/pyridine, add methanesulfonyl chloride (1.5 mmol) and stir at room temperature for 18 hours. After this time, wash the reaction with 1N hydrochloric acid while extracting with dichloromethane. Purify the title compound via radial chromatography eluting with ethyl acetate and hexane.

Workup

  1. washAfter this time, wash
  2. customthe reaction with 1N hydrochloric acid
  3. extractionwhile extracting with dichloromethane
  4. customPurify the title compound via radial chromatography
  5. washeluting with ethyl acetate and hexane

Sources & evidence

ORD record
ord-d5633abad5b3482b8b5187fc02153b40
Source dataset
uspto-grants-2011_08
Patent number
US08008301B2

Reaction notes

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