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

HRID 1428726Notes

Reaction equation

HRID 1428726 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH2:9])=[C:4]([F:10])[CH:3]=1.[CH3:11][S:12](Cl)(=[O:14])=[O:13]>N1C=CC=CC=1.ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][S:12]([CH3:11])(=[O:14])=[O:13])=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 3770848(4-Bromo-2-fluorophenyl)methanamine

Product 1

HCID 70847718N-(4-bromo-2-fluorobenzyl)methanesulfonamideYield 94.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (4-bromo-2-fluorophenyl)methanamine (5.834 g, 28.592 mmol) in pyridine were added methanesulfonyl chloride (4.2 mL, 54.325 mmol) at 0° C. The reaction mixture was stirred for 1 h, then diluted with dichloromethane. The mixture was washed with water. The organic layer was dried over magnesium sulfate and filtered. The filtrate was removed in vacuo. The crude was purified by column chromatography to give N-(4-bromo-2-fluorobenzyl)methanesulfonamide (7.597 g, 93%).

Workup

  1. washThe mixture was washed with water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate was removed in vacuo
  5. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-fda0fefbfce740f4b2ea26824f85dd6e
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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