Реакция #80193

Уравнение реакции

Ethyl 2-chloro-nicotinate

4-trifluoromethylphenylboronic acid

sodium carbonate

→

brown oil

Выход 109.7%

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

Выход 109.7%

Растворители

dimethoxyethane

dimethoxyethane

Условия реакции

Обработка

1. 1
   Другоеthe reaction vessel purged
2. 2
   ТемператураThe reaction mixture was heated at 90 C
3. 3
   Температураfor 1.5 h before being cooled
4. 4
   Экстракцияextracted with 150 ml of ether
5. 5
   ПромывкаThe organic layer was washed with 50 ml of 2N NaOH, 2×50 ml water, and brine
6. 6
   Сушкаbefore being dried (magnesium sulfate)
7. 7
   Фильтрацияfiltered
8. 8
   Концентрированиеconcentrated under vacuum

Методика

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.

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