Reaktion #476859

Reaktionsgleichung

Phenyl-methanethiol

DIPEA

xantphos

2,6-dibromotoluene

→

1-Benzylsulfanyl-3-bromo-2-methyl-benzene

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched by the addition of 150 ml of H2O
2. 2
   ExtraktionAfter extraction (three times) with ethyl acetate
3. 3
   Waschenthe combined organic layers were washed with water
4. 4
   Trocknendried with Na2SO4
5. 5
   Sonstigeevaporated to dryness
6. 6
   Sonstigethe product was purified by silica gel chromatography

Vorschrift

2,6-dibromotoluene (20 g, 100 mmol) in dioxane (160 ml) was stirred under argon. Then, DIPEA (30.9 ml, 160 mmol), xantphos (2.77 g, 4.8 mmol) and Pd2(dba)3 (2.4 g, 2.4 mmol) were added and the reaction was heated to 100° C. Phenyl-methanethiol (9.4 ml, 80 mmol) was slowly added and the reaction stirred for 6 h. The reaction was quenched by the addition of 150 ml of H2O. After extraction (three times) with ethyl acetate, the combined organic layers were washed with water, dried with Na2SO4, evaporated to dryness and the product was purified by silica gel chromatography.

Quelle