Reaktion #159434

Reaktionsgleichung

3-bromo-4′-chloro-4-ethylbiphenyl

bicyclo[3.2.1]octane-2,4-dione

2-dicyclohexylphosphino-2′,4′,6′-tri-iso-propyl-1,1′-biphenyl

potassium phosphate

→

3-(4′-chloro-4-ethylbiphen-3-yl)bicyclo[3.2.1]octane-2,4-dione

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONis added
2. 2
   Sonstigedegassed dimethoxyethane (2 ml)
3. 3
   Temperaturcooled to room temperature
4. 4
   Waschenwashed with 2M hydrochloric acid (2 ml)
5. 5
   Extraktionextracted with ethyl acetate (3×3 ml)
6. 6
   TrocknenThe organic phase is dried over magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenthe filtrate concentrated in vacuo
9. 9
   SonstigeThe crude mixture is purified by flash column chromatography on silica gel (30% to 100% ethyl acetate/hexane eluant ratio)

Vorschrift

To a microwave vial containing bicyclo[3.2.1]octane-2,4-dione (0.112 g, 0.812 mmol), palladium (II) acetate (7.6 mg, 0.034 mmol), 2-dicyclohexylphosphino-2′,4′,6′-tri-iso-propyl-1,1′-biphenyl (24.2 mg, 0.051 mmol), and finely ground potassium phosphate (0.316 g, 1.49 mmol) is added degassed dimethoxyethane (2 ml), then 3-bromo-4′-chloro-4-ethylbiphenyl (0.200 g, 0.667 mmol). This reaction mixture is then heated at 160° C. under microwave irradiation for 60 minutes, then cooled to room temperature and washed with 2M hydrochloric acid (2 ml) and extracted with ethyl acetate (3×3 ml). The organic phase is dried over magnesium sulfate, filtered, and the filtrate concentrated in vacuo. The crude mixture is purified by flash column chromatography on silica gel (30% to 100% ethyl acetate/hexane eluant ratio) to afford 3-(4′-chloro-4-ethylbiphen-3-yl)bicyclo[3.2.1]octane-2,4-dione.

Quelle