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

HRID 72571

Reaktionsgleichung

Reaktionsgleichung von HRID 72571
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].[O:12]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]([C:22](=[O:27])[C:23]([F:26])([F:25])[F:24])[CH2:14][CH2:13]1.[Al+3].[Cl-].[Cl-].[Cl-]>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([C:20]1[CH:19]=[CH:18][C:17]2[O:12][CH2:13][CH2:14][N:15]([C:22](=[O:27])[C:23]([F:25])([F:24])[F:26])[C:16]=2[CH:21]=1)=[O:8]

Komponenten

5

Edukt 3

HCID 27568715-Bromo-2-chlorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 15171868HCID 15171868, Verbindung

Produkt 1

HCID 866551971-[6-(5-Bromo-2-chloro-benzoyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To an ice cooled solution of 5-bromo-2-chlorobenzoyl chloride in dichloromethane (35 mL) was added 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) followed by AlCl3 (5.61 g, 42.2 mmol) portion wise. After 2 h, the reaction mixture was brought to room temperature and stirred overnight. The reaction was quenched by pouring it over crushed ice. The resulting mixture was extracted with dichloromethane. The organic layer was washed with aq. NaHCO3 (100 mL) and water (100 mL), and the solvent was evaporated to yield the crude product which was recrystallized from hot ethylacetate to furnish 1-[6-(5-bromo-2-chloro-benzoyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone (10.0 g).

Aufarbeitung

  1. customwas brought to room temperature
  2. customThe reaction was quenched
  3. additionby pouring it
  4. customover crushed ice
  5. extractionThe resulting mixture was extracted with dichloromethane
  6. washThe organic layer was washed with aq. NaHCO3 (100 mL) and water (100 mL)
  7. customthe solvent was evaporated
  8. customto yield the crude product which
  9. customwas recrystallized from hot ethylacetate

Quellen und Nachweise

ORD-Eintrag
ord-989649abcefc4b8a9102d99a8a2c308c
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828951B2

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