반응 #80193

반응 방정식

Ethyl 2-chloro-nicotinate

4-trifluoromethylphenylboronic acid

sodium carbonate

→

brown oil

수율 109.7%

2-(4-Trifluoromethyl-phenyl)-nicotinic acid ethyl ester

수율 109.7%

용매

dimethoxyethane

dimethoxyethane

반응 조건

후처리

1. 1
   기타the reaction vessel purged
2. 2
   온도The reaction mixture was heated at 90 C
3. 3
   온도for 1.5 h before being cooled
4. 4
   추출extracted with 150 ml of ether
5. 5
   세척The organic layer was washed with 50 ml of 2N NaOH, 2×50 ml water, and brine
6. 6
   건조before being dried (magnesium sulfate)
7. 7
   여과filtered
8. 8
   농축concentrated under vacuum

실험 절차

Ethyl 2-chloro-nicotinate (1.86 g, 10.0 mmol) was dissolved in 10 ml of dimethoxyethane. Tetrakis(triphenylphosphine)palladium (347 mg, 0.3 mmol) was added and the reaction vessel purged by alternating vacuum and nitrogen gas three times. A solution of 4-trifluoromethylphenylboronic acid (2.09 g, 11.0 mmol) in 20 ml of dimethoxyethane was added to the reaction mixture followed by 10 ml of a 2M sodium carbonate solution. The reaction mixture was heated at 90 C. for 1.5 h before being cooled and extracted with 150 ml of ether. The organic layer was washed with 50 ml of 2N NaOH, 2×50 ml water, and brine before being dried (magnesium sulfate), filtered and concentrated under vacuum to afford 3.24 g of a brown oil. This material was purified by silica gel chromatography eluting with 5 to 10% ethyl acetate in hexanes to afford 2.34 g of the title compound as a pale yellow oil.

출처