4-Fluoro-2-nitroaniline → HCID 68951721, compound

HRID 730237Notes

Reaction equation

HRID 730237 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[Br:12][C:13]1[CH:14]=[CH:15][C:16]([O:23][CH3:24])=[C:17]([S:19](Cl)(=[O:21])=[O:20])[CH:18]=1>N1C=CC=CC=1.C(OCC)(=O)C>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([O:23][CH3:24])=[C:17]([S:19]([NH:6][C:5]2[CH:7]=[CH:8][C:2]([F:1])=[CH:3][C:4]=2[N+:9]([O-:11])=[O:10])(=[O:20])=[O:21])[CH:18]=1

Participants

5

Reactant 2

HCID 677694-Fluoro-2-nitroanilineHCID 5200205-Bromo-2-methoxybenzene-1-sulfonyl chloride

Product 1

HCID 68951721HCID 68951721, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-fluoro-2-nitroaniline (1 mmol) in pyridine (3 mL), 5-bromo-2-methoxybenzenesulfonyl chloride (1.2 mmol) was added and the resulting mixture was stirred at room temperature for 24 h. The reaction mixture was diluted with ethyl acetate (20 mL). The contents were washed with 10% aqueous HCl (20 mL) and brine (20 mL), dried over sodium sulfate, and concentrated under vacuum. The residue obtained was purified by column chromatography eluting with hexanes/ethyl acetate to give 223 mg of 5-bromo-N-(4-fluoro-2-nitrophenyl)-2-methoxybenzenesulfonamide.

Workup

  1. washThe contents were washed with 10% aqueous HCl (20 mL) and brine (20 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue obtained
  5. customwas purified by column chromatography
  6. washeluting with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-b2275ade5d69431fbfd0daac402b3f9f
Source dataset
uspto-grants-2009_09
Patent number
US07582673B2

Reaction notes

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