Реакция #91064

Уравнение реакции

cyclopentylmagnesium chloride

methyl 4-chloro-3-(trifluoromethyl)benzoate

→

title compound

Выход 95.8%

Methyl 4-Cyclopentyl-3-(trifluoromethyl)benzoate

Выход 95.8%

Условия реакции

Обработка

1. 1
   ТемператураThe mixture was heated
2. 2
   Температураunder reflux for 2 h
3. 3
   Температураto cool to room temperature
4. 4
   Другоеquenched with saturated aqueous sodium bicarbonate solution
5. 5
   Фильтрацияfiltered
6. 6
   ЭкстракцияThe filtrate was extracted with ethyl acetate
7. 7
   СушкаThe organic layer was dried over anhydrous sodium sulfate
8. 8
   Концентрированиеconcentrated under reduced pressure
9. 9
   Другоеpurified by silica gel column chromatography

Методика

To zinc(II) chloride (0.5 M solution in tetrahydrofuran, 88.0 mL, 44.0 mmol) was added cyclopentylmagnesium chloride (2 M solution in ether, 20.5 mL, 41.1 mmol). The resulting suspension was stirred at room temperature for 1 h. To the above suspension was added methyl 4-chloro-3-(trifluoromethyl)benzoate (7.00 g, 29.3 mmol) and bis(tri-tert-butylphosphine)palladium (1.35 g, 2.64 mmol) at room temperature. The mixture was heated under reflux for 2 h. The mixture was allowed to cool to room temperature, quenched with saturated aqueous sodium bicarbonate solution and filtered. The filtrate was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure and purified by silica gel column chromatography to give the title compound as an oil (7.64 g). LCMS m/z=273.2 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.57-1.66 (m, 2H), 1.68-1.82 (m, 2H), 1.82-1.94 (m, 2H), 2.04-221 (m, 2H), 3.33-3.49 (m, 1H), 3.93 (s, 3H), 7.54 (d, J=8.21 Hz, 1H), 8.13 (dd, J=8.34, 1.77 Hz, H), 8.27 (s, 1H).

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