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 1695817Notes

Reaction equation

HRID 1695817 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-af5d8818aa9f40828b54e0743f7a8711
Source dataset
uspto-grants-2012_04
Patent number
US08163704B2

Reaction notes

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