p-Fluoronitrobenzene → HCID 14933055, Verbindung

HRID 1030278

Reaktionsgleichung

Reaktionsgleichung von HRID 1030278
CC([O-])(C)C.[K+].F[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1.[Cl:17][CH2:18][CH2:19][CH2:20][SH:21]>CS(C)=O.O>[Cl:17][CH2:18][CH2:19][CH2:20][S:21][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1

Komponenten

6

Edukt 3

HCID 9590p-FluoronitrobenzeneHCID 871343-ChloropropanethiolHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 14933055HCID 14933055, VerbindungAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittel2×HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

To a cooled (10° C.), stirred suspension of KOtBu (8.9 g, 0.080 mol) in DMSO (40 mL) was added a solution of 4-fluoronitrobenzene (11.2 g, 0.080 mol) and 3-chloropropanethiol (8.8 g, 0.080 mol) in DMSO (40 mL) over 10 minutes. The mixture was stirred at room temperature for 3.5 hours, diluted with water (1000 ml), and extracted with ether. The extracts were washed with brine, dried (MgSO4), and concentrated. Purification by flash chromatography (10% EtOAc/hexane) gave 6.2 g (34%) of product as a yellow solid m.p. 45°-48° C.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 3.5 hours
  2. extractionextracted with ether
  3. washThe extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customPurification by flash chromatography (10% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-7e3d4cb3d6324a3a900fd6ef81d27707
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05104892

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