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 1258809Notes

Reaction equation

HRID 1258809 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:3][CH2:2]1.[Br:17][C:18]1[CH:19]=[CH:20][C:21]([Cl:27])=[C:22]([CH:26]=1)[C:23](Cl)=[O:24].[Al+3].[Cl-].[Cl-].[Cl-]>ClCCl>[Br:17][C:18]1[CH:19]=[CH:20][C:21]([Cl:27])=[C:22]([CH:26]=1)[C:23]([C:9]1[CH:8]=[CH:7][C:6]2[O:1][CH2:2][CH2:3][N:4]([C:11](=[O:16])[C:12]([F:15])([F:13])[F:14])[C:5]=2[CH:10]=1)=[O:24]

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-ethanoneYield 79.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  1. customwas brought to room temperature
  2. customThe reaction was quenched
  3. additionby pouring
  4. customover crushed ice
  5. extractionextracted with dichloromethane (2×50 mL)
  6. washThe organic layer was washed with aq. NaHCO3 (30 mL), H2O (20 mL)
  7. customthe solvent evaporated
  8. customto get the crude product which
  9. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2f594b71c1e041d7a34b4113b9a2fa4c
Source dataset
uspto-grants-2013_06
Patent number
US08466114B2

Reaction notes

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