Реакция #159754

Уравнение реакции

1-[6-(5-bromo-2-chloro-benzoyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone

BF3.OEt2

Et3SiH

→

1-[6-(5-bromo-2-chloro-benzyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone

Выход 85.9%

Растворители

1,2-dichloroethane MeCN

Условия реакции

Обработка

1. 1
   Другоеthen quenched by the addition of aq. NaHCO3 (˜200 mL)
2. 2
   ЭкстракцияThe resulting mixture was extracted with ethyl acetate (3×200 mL)
3. 3
   Промывкаthe combined organic layers were washed with brine (200 mL)
4. 4
   Сушкаdried over sodium sulfate
5. 5
   ДругоеCrude product obtained
6. 6
   Другоеafter evaporation of solvent
7. 7
   Другоеwas purified by silica gel column chromatography

Методика

To a stirred solution of 1-[6-(5-bromo-2-chloro-benzoyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone (36 g, 80.35 mmol) in 1,2-dichloroethane:MeCN 1:2 (180 mL) was added BF3.OEt2 (13.2 mL, 104 mmol) and Et3SiH (26.9 mL, 168.7 mmol) at 0° C. The reaction mixture was stirred overnight at room temperature then quenched by the addition of aq. NaHCO3 (˜200 mL). The resulting mixture was extracted with ethyl acetate (3×200 mL), and the combined organic layers were washed with brine (200 mL) and dried over sodium sulfate. Crude product obtained after evaporation of solvent was purified by silica gel column chromatography to furnish 1-[6-(5-bromo-2-chloro-benzyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone (30 g).

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