반응 #67702

반응 방정식

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

cyclopropyl boronic acid

tri-potassium phosphate monohydrate

tricyclohexyl phosphine

→

title compound

수율 71.0%

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

수율 71.0%

용매

Water

toluene

water

반응 조건

후처리

1. 1
   기타overnight
2. 2
   기타at room temperature
3. 3
   온도The mixture was cooled to room temperature
4. 4
   추출the mixture extracted with ethyl acetate
5. 5
   세척The organic layer was washed once with brine
6. 6
   건조dried over sodium sulfate
7. 7
   여과filtered
8. 8
   농축concentrated in vacuo
9. 9
   기타The crude compound was purified on silica gel (eluent: heptane/ethyl acetate 0 to 10%)

실험 절차

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.

출처