Реакция #359861

Уравнение реакции

water

mixture

4-chloro-1-iodo-2-methoxybenzene

DMF

→

desired product

Выход 90.0%

4-chloro-2-methoxybenzonitrile

Выход 90.0%

Условия реакции

Обработка

1. 1
   Экстракцияextracted with ethyl acetate several times
2. 2
   ПромывкаThe combined extracts were washed with water and brine
3. 3
   Сушкаdried (MgSO4)
4. 4
   Фильтрацияfiltered
5. 5
   Концентрированиеconcentrated under vacuum
6. 6
   ДругоеThe residue was purified by flash column chromatography on silica gel with 9:1 hexanes/ethyl acetate

Методика

A mixture of Example 59A (2.68 g, 10 mmol), Zn(CN)2 (0.654 g, 5.5 mmol), and Pd(PPh3)4 (0.577 g, 0.5 mmol) in DMF (15 mL) was stirred at 90° C. for 6 hours and cooled to room temperature. The reaction mixture was poured into water (500 mL) and extracted with ethyl acetate several times. The combined extracts were washed with water and brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel with 9:1 hexanes/ethyl acetate to provide 1.34 g (90%) of the desired product. MS (DCI) m/e 168 (M+H)+; 1H NMR (300 MHz, CDCl3) δ 7.49 (d, J=8.1 Hz, 1H), 6.97-7.03 (m, 2H).

Источник