Reaktion #159747

Reaktionsgleichung

1-(2,3-dihydro-benzo[1,4]oxazin-4-yl)-2,2,2-trifluoro-ethanone

5-bromo-2-chlorobenzoyl chloride

AlCl3

→

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

Ausbeute 79.3%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas brought to room temperature
2. 2
   SonstigeThe reaction was quenched
3. 3
   workup.ADDITIONby pouring
4. 4
   Sonstigeover crushed ice
5. 5
   Extraktionextracted with dichloromethane (2×50 mL)
6. 6
   WaschenThe organic layer was washed with aq. NaHCO3 (30 mL), H2O (20 mL)
7. 7
   Sonstigethe solvent evaporated
8. 8
   Sonstigeto get the crude product which
9. 9
   Sonstigewas purified by silica gel column chromatography

Vorschrift

To a stirred solution of 1-(2,3-dihydro-benzo[1,4]oxazin-4-yl)-2,2,2-trifluoro-ethanone (6.5 g, 28.1 mmol) in dichloromethane (45 mL) was added 5-bromo-2-chlorobenzoyl chloride (8.54 g, 33.7 mmol) in dichloromethane (35 mL) and AlCl3 (5.61 g, 42.2 mmol) at 0° C. After 2 h, the reaction mixture was brought to room temperature and stirred overnight. The reaction was quenched by pouring over crushed ice and extracted with dichloromethane (2×50 mL). The organic layer was washed with aq. NaHCO3 (30 mL), H2O (20 mL), and the solvent evaporated to get the crude product which was purified by silica gel column chromatography to give 1-[6-(5-bromo-2-chloro-benzoyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone (10.0 g).

Quelle