Dimethylamine → 4-bromo-2-fluoro-N,N-dimethylbenzenesulfonamide

HRID 83753Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 83753
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[C:4]([F:12])[CH:3]=1.C[CH2:14][N:15](CC)[CH2:16]C.CNC.C1COCC1>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:15]([CH3:16])[CH3:14])(=[O:10])=[O:9])=[C:4]([F:12])[CH:3]=1

Komponenten

6

Edukt 4

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 27363104-Bromo-2-fluorobenzene-1-sulfonyl chloride

Produkt 1

HCID 592067474-bromo-2-fluoro-N,N-dimethylbenzenesulfonamideAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To 4-bromo-2-fluorobenzene-1-sulfonyl chloride (1.0 g, 3.7 mmol) and Et3N (1.5 mL, 11 mmol) in dichloromethane (10 mL) was added a solution of dimethylamine 2.0 M in THF (2.2 mL, 4.4 mmol). The reaction was stirred at ambient temperature for 30 minutes. The reaction was washed with 10 mL of 1N aqueous HCl and 10 mL of brine. Organics were dried over Na2SO4 and evaporated to dryness. Crude product was purified by chromatography on silica gel (eluting with 0-25% ethyl acetate in hexanes) to afford 4-bromo-2-fluoro-N,N-dimethylbenzenesulfonamide (780 mg, 75%).

Aufarbeitung

  1. washThe reaction was washed with 10 mL of 1N aqueous HCl and 10 mL of brine
  2. dry with materialOrganics were dried over Na2SO4
  3. customevaporated to dryness
  4. customCrude product was purified by chromatography on silica gel (eluting with 0-25% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-3e0b2a28cb8c4daf9445f3578e7c0b79
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846753B2

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