Water → HCID 21797966, compound

HRID 1985818Notes

Reaction equation

HRID 1985818 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6]#[N:7].B(Br)(Br)Br.O>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:6]#[N:7]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 23143900HCID 23143900, compound

Product 1

HCID 21797966HCID 21797966, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Methoxy-4-phenylbenzonitrile (17.8 g) was dissolved in dichloromethane (200 mL). To the stirred mixture was added dropwise boron tribromide (14 mL) under ice-cooling, and the mixture was stirred at continuous temperature for 6 hours. To the stirred reaction mixture was added dropwise water (200 mL) under ice-cooling, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/5) to give the title compound (11.0 g).

Workup

  1. temperaturecooling
  2. customTo the stirred reaction mixture
  3. temperaturecooling
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/5)

Sources & evidence

ORD record
ord-06bd0748f77a4e5795ac0f5485e10374
Source dataset
uspto-grants-2009_06
Patent number
US07547680B2

Reaction notes

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