Reaktion #2142952

Reaktionsgleichung

α-bromobenzeneacetonitrile

bromide

Water

carbon disulfide

→

α-cyanobenzyl 4-methyldithiobenzoate

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture stirred for another 2 h
2. 2
   Extraktionthe organic product was extracted with diethyl ether (3×50 ml)
3. 3
   Trocknendried with magnesium sulfate overnight
4. 4
   Filtrationfiltered
5. 5
   SonstigeAfter removal of solvent and column chromatography (5:2 mixture of hexane and ethyl ether)

Vorschrift

To a 100 ml round bottom flask was added 10 ml 4-tolylmagiesium bromide (1.0M solution in ethyl ether) and diluted to 20 ml with anhydrous THF. 0.76 g carbon disulfide was added dropwise to this mixture and stirred for ½ h at room temperature. Then to the dark red solution was added 2 g α-bromobenzeneacetonitrile dropwise and the mixture stirred for another 2 h. Water was added to the mixture and the organic product was extracted with diethyl ether (3×50 ml), dried with magnesium sulfate overnight and filtered. After removal of solvent and column chromatography (5:2 mixture of hexane and ethyl ether), pure α-cyanobenzyl 4-methyldithiobenzoate was obtained as a red odorless solid (48% yield). Proton and carbon NMR spectra were consistent with the expected structure, CTA-CP-6.

Quelle