Chlorosulfonic acid → 3-Bromo-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chloride

HRID 1044714Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1044714
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11].[Cl:15][S:16](O)(=[O:18])=[O:17]>>[Br:1][C:2]1[CH:7]=[C:6]([S:16]([Cl:15])(=[O:18])=[O:17])[CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:14])[C:10]([F:13])([F:11])[F:12]

Komponenten

3

Edukt 2

HCID 24638Chlorosulfonic acidHCID 4263215N-(2-Bromophenyl)-2,2,2-trifluoroacetamide

Produkt 1

HCID 581587063-Bromo-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chlorideAusbeute 80 %

Versuchsvorschrift

3.0 g N-(2-Bromo-phenyl)-2,2,2-trifluoro-acetamide was added in three portions to 3.74 mL (5.0 equiv.) chlorosulfonic acid under cooling in an ice-bath. The ice-bath was removed, the mixture was warmed to room temperature, and subsequently stirred for 1 hour at 80° C. After cooling, the clear brown reaction mixture was poured into ice and extracted with DCM. The organic phase was dried over Na2SO4, filtered, and evaporated to dryness to give 3.36 g (80%) of an oil that solidified upon standing. 1H NMR (400 MHz, CDCl3) δ 8.09 (dd, J=9.0, 2.0 Hz, 1H), 8.30 (d, J=2.0 Hz, 1H), 8.69 (d, J=9.0 Hz, 1H), 8.71 (br.s., 1H).

Aufarbeitung

  1. temperatureunder cooling in an ice-bath
  2. customThe ice-bath was removed
  3. temperatureAfter cooling
  4. additionthe clear brown reaction mixture was poured into ice
  5. extractionextracted with DCM
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-4b328f8b9f46486892d914bbfdbac6fd
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563723B2

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