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

HRID 876128
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 876128
[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
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Komponenten

5

Edukt 3

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

Produkt 1

HCID 67066531N-(4-bromo-2-fluoro-5-methylphenyl)methanesulfonamideAusbeute 99,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-2850328cd2a14aebb4c42b784d9a12ed
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08986740B2

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