Reaktion #489989

Reaktionsgleichung

4-bromo-2-chlorobenzenethiol

Cs2CO3

3-methylbut-3-en-1-yl diphenyl phosphate

→

desired product

4-bromo-2-chloro-1-[(3-methylbut-3-en-1-yl)sulfanyl]benzene

Lösungsmittel

DMF

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigesynthesized
2. 2
   Temperaturto cool to room temperature
3. 3
   ExtraktionThe resulting mixture was extracted with EtOAc
4. 4
   Trocknenhexanes mixture (1:1, 75.0 mL, 2×) and the combined organic layers were dried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated under vacuum
7. 7
   SonstigeThe crude mixture was purified by silica gel chromatography
8. 8
   Wascheneluting with 0-10% EtOAc/hexanes

Vorschrift

To a mixture of 4-bromo-2-chlorobenzenethiol (1.68 g, 7.54 mmol) and Cs2CO3 (4.09 g, 12.6 mmol) in DMF (8.98 mL) at room temperature was added 3-methylbut-3-en-1-yl diphenyl phosphate (2.00 g, 6.28 mmol, synthesized according to a procedure in U.S. Pat. No. 5,006,550, 9 Apr. 1991) dropwise via a syringe. The reaction mixture was heated to 85° C. for 1 hour. It was then allowed to cool to room temperature and diluted with water (20.0 mL). The resulting mixture was extracted with EtOAc:hexanes mixture (1:1, 75.0 mL, 2×) and the combined organic layers were dried over Na2SO4, filtered and concentrated under vacuum. The crude mixture was purified by silica gel chromatography eluting with 0-10% EtOAc/hexanes to give the desired product as a colorless oil.

Quelle