1-Bromo-3-chloropropane → Toluene-4-thiosulfonic acid S-(3-chloropropyl)ester

HRID 707674Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 707674
[S:1]([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([O-:4])(=[O:3])=[S:2].[K+].Br[CH2:14][CH2:15][CH2:16][Cl:17]>CC(C)=O>[Cl:17][CH2:16][CH2:15][CH2:14][S:2][S:1]([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Komponenten

4

Edukt 2

HCID 80061-Bromo-3-chloropropaneHCID 23662126Benzenesulfonothioic acid, 4-methyl-, potassium salt (1:1)

Produkt 1

HCID 67607671Toluene-4-thiosulfonic acid S-(3-chloropropyl)ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Potassium thiotosylate (50.0 g, 221 mmol, 1.0 eq.) and 1-bromo-3-chloropropane (38.0 g, 241 mmol, 1.09 eq.) were stirred together in acetone (1 L) at room temperature for 72 hours. The mixture was then concentrated. Next, the mixture was partitioned between dichloromethane and water. The organic solution was washed with brine (2×), dried using MgSO4, concentrated and azeotroped with toluene to produce a pale yellow oil weighing 54 g (92%).

Aufarbeitung

  1. concentrationThe mixture was then concentrated
  2. customNext, the mixture was partitioned between dichloromethane and water
  3. washThe organic solution was washed with brine (2×)
  4. customdried
  5. concentrationconcentrated
  6. customazeotroped with toluene
  7. customto produce a pale yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-0426f9cb8c95443eafe75af8829db2b2
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09175042B2

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