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

HRID 1428722Notes

Reaction equation

HRID 1428722 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 was 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 removed in vacuo. The crude was purified by column chromatography. N-(4-bromo-2-fluorobenzyl)methanesulfonamide (7.597 g) was obtained as 93% yield.

Workup

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

Sources & evidence

ORD record
ord-6db461efc2d94a5da7a413f9b4cebbf5
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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