Реакция #359860

Уравнение реакции

solution

4-chloro-1-iodo-2-methoxybenzene

triethylamine

n-butyl vinyl ether

→

desired product

Выход 65.0%

1-(4-chloro-2-methoxyphenyl)ethanone

Выход 65.0%

Растворители

DMF

Условия реакции

Обработка

1. 1
   Другоеpurged with nitrogen
2. 2
   Температураcooled to room temperature
3. 3
   Другоеpartitioned between ethyl acetate and water
4. 4
   ЭкстракцияThe aqueous layer was extracted with ethyl acetate
5. 5
   Промывкаthe combined organic layers were washed with water and brine
6. 6
   Сушкаdried (MgSO4)
7. 7
   Фильтрацияfiltered
8. 8
   Концентрированиеconcentrated under vacuum
9. 9
   ДругоеThe residue was purified by flash column chromatography on silica gel with 4:1 hexanes/ethyl acetate

Методика

A solution of Example 59A (2.68 g, 10 mmol) in DMF (40 mL) was treated with triethylamine (1.53 mL, 11 mmol), n-butyl vinyl ether (6.5 mL, 50 mmol), DPPF (554 mg, 1 mmol) and Pd(OAc)2 (112 mg, 0.5 mmol), purged with nitrogen, heated to 80° C. for 6 hours, cooled to room temperature, and partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate, and the combined organic layers 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 4:1 hexanes/ethyl acetate to provide 1.20 g (65%) of the desired product. MS (ESI) m/e 185 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 7.60 (d, J=8.14 Hz, 1H), 7.27 (d, J=1.70 Hz, 1H), 7.09 (dd, J=8.31, 1.86 Hz, 1H), 3.92 (s, 3H).

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