Methanesulfonyl chloride → HCID 4686460, compound

HRID 2390811Notes

Reaction equation

HRID 2390811 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[F:9].[CH3:10][S:11](Cl)(=[O:13])=[O:12]>N1C=CC=CC=1.CCOC(C)=O>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][S:11]([CH3:10])(=[O:13])=[O:12])=[CH:4][C:3]=1[F:9]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 8218484-Bromo-3-fluoroaniline

Product 1

HCID 4686460HCID 4686460, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

step 1—To a solution of 4-bromo-3-fluoro-aniline (1.00 g, 5.263 mmol) in pyridine (5 mL) at 0° C. was added methanesulfonyl chloride (0.500 mL, 6.424 mmol). The reaction was gradually warmed to RT and stirred overnight then diluted with EtOAc. The organic layer was washed successively with saturated aqueous CuSO4 solution, brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (5 to 20% EtOAc) to afford 1.235 g (88%) of N-(4-bromo-3-fluoro-phenyl)-methanesulfonamide (72) as a white solid.

Workup

  1. washThe organic layer was washed successively with saturated aqueous CuSO4 solution, brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by SiO2 chromatography
  6. washeluting with an EtOAc/hexane gradient (5 to 20% EtOAc)

Sources & evidence

ORD record
ord-8b9143bd37084c73b824ab3bc6080ea8
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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