Reaktion #159754

Reaktionsgleichung

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

Ausbeute 85.9%

Lösungsmittel

1,2-dichloroethane MeCN

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethen quenched by the addition of aq. NaHCO3 (˜200 mL)
2. 2
   ExtraktionThe resulting mixture was extracted with ethyl acetate (3×200 mL)
3. 3
   Waschenthe combined organic layers were washed with brine (200 mL)
4. 4
   Trocknendried over sodium sulfate
5. 5
   SonstigeCrude product obtained
6. 6
   Sonstigeafter evaporation of solvent
7. 7
   Sonstigewas purified by silica gel column chromatography

Vorschrift

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).

Quelle