Pyridine → N-(4-bromo-2-fluoro-5-methylphenyl)methanesulfonamide

HRID 508377Notes

Reaction equation

HRID 508377 reaction equation
[Br:1][C:2]1[C:8]([CH3:9])=[CH:7][C:5]([NH2:6])=[C:4]([F:10])[CH:3]=1.N1C=CC=CC=1.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C(Cl)Cl>[Br:1][C:2]1[C:8]([CH3:9])=[CH:7][C:5]([NH:6][S:18]([CH3:17])(=[O:20])=[O:19])=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 70180404-Bromo-2-fluoro-5-methylaniline

Product 1

HCID 67066531N-(4-bromo-2-fluoro-5-methylphenyl)methanesulfonamideYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-2-fluoro-5-methylaniline (2.04 g, 10.0 mmol) in anhydrous CH2Cl2 (20 ml) and pyridine (3.23 ml, 40.0 mmol) was added methanesulfonyl chloride (0.86 ml, 11.0 mmol) and the resulting mixture was stirred at room temperature for 2 h. Solvent was removed in vacuo, and the residue was partitioned between EtOAc and 1M aq. HCl. The organic layer was washed with saturated aqueous NaHCO3, brine and then dried over Na2SO4. The drying agent was filtered off, and the filtrate was concentrated to give the title compound as a solid (2.80 g, 99%).

Workup

  1. customSolvent was removed in vacuo
  2. customthe residue was partitioned between EtOAc and 1M aq. HCl
  3. washThe organic layer was washed with saturated aqueous NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. filtrationThe drying agent was filtered off
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7d69ab1ae8984a59bece8de8553b4c72
Source dataset
uspto-grants-2015_08
Patent number
US09095590B2

Reaction notes

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