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

HRID 238937Notes

Reaction equation

HRID 238937 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([CH:9]=[CH2:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:11][S:12](Cl)(=[O:14])=[O:13]>N1C=CC=CC=1.O>[F:1][C:2]1[CH:8]=[C:7]([CH:9]=[CH2:10])[CH:6]=[CH:5][C:3]=1[NH:4][S:12]([CH3:11])(=[O:14])=[O:13]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 220256474-Ethenyl-2-fluoroaniline

Product 1

HCID 69527926N-(4-Ethenyl-2-fluorophenyl)methanesulfonamideYield 91.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A cooled solution of 2-Fluoro-4-vinylaniline (20-1, 0.96 g, 7 mmol) in pyridine (10 mL) at 0° C. was treated with methanesulfonyl chloride (0.644 mL, 8.4 mmol) and stirred at room temperature for 30 min. The reaction mixture was diluted with water and extracted with EtOAc several times. The combined organic layers were washed with water and brine, dried over MgSO4, filtered, and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes (1:3) as eluant to afford N-(2-Fluoro-4-vinylphenyl)methanesulfonamide (20-2, LJO-325, 1.372 g, 91%) as a white solid.

Workup

  1. extractionextracted with EtOAc several times
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-10143971cf754a20be9943368f404851
Source dataset
uspto-grants-2014_02
Patent number
US08642657B2

Reaction notes

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