Reaktion #820018

Reaktionsgleichung

water

potassium tert-butoxide

4-bromo-benzenethiol

cyclopropyl bromide

→

1-bromo-4-cyclopropylsulfanyl-benzene

Ausbeute 72.0%

Lösungsmittel

DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISSOLUTIONuntil dissolved
2. 2
   Sonstigethe reaction to 80° C. for 2 days
3. 3
   workup.ADDITIONpour
4. 4
   ExtraktionExtract the aqueous layer with Et2O (2×200 mL)
5. 5
   Waschenwash the combined organic layers with water (100 mL)
6. 6
   TrocknenDry over sodium sulfate
7. 7
   Einengenconcentrate in vacuo
8. 8
   WaschenChromatograph the residue on a SiO2 column eluting the material with hexanes

Vorschrift

Dissolve 4-bromo-benzenethiol (2.00 g, 10.6 mmol) in dry DMSO (50 mL) under a nitrogen atmosphere. Add potassium tert-butoxide (1.30 g, 11.7 mmol) and stir until dissolved. Add cyclopropyl bromide (2.6 mL, 31.8 mmol) and heat the reaction to 80° C. for 2 days. Cool to room temperature and pour the reaction into water (500 mL). Extract the aqueous layer with Et2O (2×200 mL) and wash the combined organic layers with water (100 mL). Dry over sodium sulfate and concentrate in vacuo. Chromatograph the residue on a SiO2 column eluting the material with hexanes to give 1.73 g of 1-bromo-4-cyclopropylsulfanyl-benzene (72%).

Quelle