Boron tribromide → HCID 140584041, compound

HRID 1619165Notes

Reaction equation

HRID 1619165 reaction equation
[CH2:1]([O:4]/[N:5]=[C:6](/[C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([O:15]C)=[CH:10][C:9]=1[CH3:17])\[CH3:7])[CH2:2][CH3:3].B(Br)(Br)Br>ClCCl.O>[CH2:1]([O:4]/[N:5]=[C:6](/[C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([OH:15])=[CH:10][C:9]=1[CH3:17])\[CH3:7])[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 88531334HCID 88531334, compound

Product 1

HCID 140584041HCID 140584041, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.5 g (2.0 mmol) of (E)-1-(4-methoxy-2,5-dimethylphenyl)ethanone-propyloxime obtained in Step 4 in 15 mL of dichloromethane was added boron tribromide (BBr3) (0.28 mL, 2.9 mmol) and the reaction mixture was allowed to react at room temperature with stirring. After completion of the reaction, the residue was stirred in water (20 mL) and the aqueous layer was extracted twice with 20 mL of dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and concentrated in a vacuum and the concentrate was purified by silica gel chromatography to afford 0.23 g of (E)-1-(4-hydroxy-2,5-dimethylphenyl)ethanone propyloxime as a white oil (yield: 49%).

Workup

  1. customto react at room temperature
  2. customAfter completion of the reaction
  3. extractionthe aqueous layer was extracted twice with 20 mL of dichloromethane
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated in a vacuum
  6. customthe concentrate was purified by silica gel chromatography

Sources & evidence

ORD record
ord-23701c6d60a849acb2213dc84ec1ea6f
Source dataset
uspto-grants-2014_07
Patent number
US08772290B2

Reaction notes

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