Reaction #67702

Reaction equation

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

cyclopropyl boronic acid

tri-potassium phosphate monohydrate

tricyclohexyl phosphine

→

title compound

Yield 71.0%

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

Yield 71.0%

Solvents

Water

toluene

water

Conditions

Workup

1. 1
   Otherovernight
2. 2
   Otherat room temperature
3. 3
   TemperatureThe mixture was cooled to room temperature
4. 4
   Extractionthe mixture extracted with ethyl acetate
5. 5
   WashThe organic layer was washed once with brine
6. 6
   Dryingdried over sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated in vacuo
9. 9
   OtherThe crude compound was purified on silica gel (eluent: heptane/ethyl acetate 0 to 10%)

Procedure

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.

Source