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

HRID 640642Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 640642
[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-ca8a4cdbafb844b096ceadf27dc5f722
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691902B2

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