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 1258815Notes

Reaction equation

HRID 1258815 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-40e2621073154272a1a976aa7eca436d
Source dataset
uspto-grants-2013_06
Patent number
US08466114B2

Reaction notes

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