Réaction #80193

Équation de réaction

Ethyl 2-chloro-nicotinate

4-trifluoromethylphenylboronic acid

sodium carbonate

→

brown oil

Rendement 109.7%

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

Rendement 109.7%

Solvants

dimethoxyethane

dimethoxyethane

Conditions de réaction

Traitement

1. 1
   Autrethe reaction vessel purged
2. 2
   TempératureThe reaction mixture was heated at 90 C
3. 3
   Températurefor 1.5 h before being cooled
4. 4
   Extractionextracted with 150 ml of ether
5. 5
   LavageThe organic layer was washed with 50 ml of 2N NaOH, 2×50 ml water, and brine
6. 6
   Séchagebefore being dried (magnesium sulfate)
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated under vacuum

Mode opératoire

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.

Source