Water → HCID 21099420, Verbindung

HRID 2376971Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2376971
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[Br:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([O-:19])=[O:18])=[CH:13][CH:12]=1.[Na+].CN(C)CCN.O>CS(C)=O>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])(=[O:19])=[O:18])=[CH:13][CH:12]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 66053N,N-DimethylethylenediamineHCID 811292-BromobenzaldehydeHCID 23670685Sodium 4-bromobenzene-1-sulfinate

Produkt 1

HCID 21099420HCID 21099420, VerbindungAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

2-Bromobenzaldehyde (1.55 g, 8.4 mmol), sodium 4-bromophenylsulfinate (2.79 g, 10 mmol) and copper(I) trifluoromethanesulfonate benzene complex (500 mg, 1 mmol) were combined in dimethylsulfoxide (10 mL) under nitrogen and degassed. The suspension was heated to 110° C. and N,N-dimethylethylenediamine (176 mg, 2 mmol) was added. The reaction was heated until the colour became clear and pale yellow, then cooled and poured into water. The products were extracted into ethyl acetate. The organic layer was washed with water:brine (1:1, ×5), dried over MgSO4 and evaporated in vacuo. The residue was triturated with isohexane to give 2-[(4-bromophenyl)sulfonyl]benzaldehyde (1.5 g, 55%). δH (400 MHz, CDCl3): 10.76 (1H, s), 8.14-8.12 (1H, m), 7.98-7.96 (1H, m), 7.76-7.68 (4H, m), 7.64-7.62 (2H, m).

Aufarbeitung

  1. customdegassed
  2. temperatureThe reaction was heated until the colour
  3. temperaturepale yellow, then cooled
  4. extractionThe products were extracted into ethyl acetate
  5. washThe organic layer was washed with water:brine (1:1, ×5)
  6. dry with materialdried over MgSO4
  7. customevaporated in vacuo
  8. customThe residue was triturated with isohexane

Quellen und Nachweise

ORD-Eintrag
ord-e1dcaa7d07224a34bfef95711daf4f48
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07468393B2

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