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

HRID 1962354Notes

Reaction equation

HRID 1962354 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-69a46295631f45c0ad5d95b7eaf6f8fe
Source dataset
uspto-grants-2013_04
Patent number
US08415351B2

Reaction notes

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