Reaktion #67702

Reaktionsgleichung

2-bromo-4-trifluoromethyl-benzoic acid methyl ester

cyclopropyl boronic acid

tri-potassium phosphate monohydrate

tricyclohexyl phosphine

→

title compound

Ausbeute 71.0%

2-Cyclopropyl-4-trifluoromethyl-benzoic acid methyl ester

Ausbeute 71.0%

Lösungsmittel

Water

toluene

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeovernight
2. 2
   Sonstigeat room temperature
3. 3
   TemperaturThe mixture was cooled to room temperature
4. 4
   Extraktionthe mixture extracted with ethyl acetate
5. 5
   WaschenThe organic layer was washed once with brine
6. 6
   Trocknendried over sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated in vacuo
9. 9
   SonstigeThe crude compound was purified on silica gel (eluent: heptane/ethyl acetate 0 to 10%)

Vorschrift

To a solution of 400 mg (1.413 mmol) 2-bromo-4-trifluoromethyl-benzoic acid methyl ester, 146 mg (1.696 mmol) cyclopropyl boronic acid, 1.21 g (4.946 mmol) tri-potassium phosphate monohydrate and 40.9 mg (0.141 mmol) tricyclohexyl phosphine in 6 ml toluene and 0.3 ml water under nitrogen at room temperature, was added 15.9 mg (0.0707 mmol) palladium acetate. The mixture was stirred in a 100° C. oil bath for 4 hours and overnight at room temperature under nitrogen. The mixture was cooled to room temperature. Water was added and the mixture extracted with ethyl acetate. The organic layer was washed once with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude compound was purified on silica gel (eluent: heptane/ethyl acetate 0 to 10%) to provide 0.24 g (71%) of the title compound as a yellow oil.

Quelle