Boron tribromide → HCID 18440061, compound

HRID 337257Notes

Reaction equation

HRID 337257 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH2:10][C:11]#[N:12])[CH:6]=[CH:7][C:8]=1[CH3:9].B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([CH2:10][C:11]#[N:12])[CH:6]=[CH:7][C:8]=1[CH3:9]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 2882193-methoxy-4-methylphenylacetonitrile

Product 1

HCID 18440061HCID 18440061, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(3-methoxy-4-methylphenyl)acetonitrile (5 g, 31 mmol) in dry CH2Cl2 (20 ml) was added drop wise BBr3 (1M in CH2Cl2, 10.02 g, 40 mmol) at −78° C. under argon. The reaction mixture was stirred at the same temperature for 2 hours and then at 0° C. for 5 hours or until all the starting material is consumed, quenched with ice, extracted with EtOAc (30 ml×3), the combined organic layer was washed carefully with sat NaHCO3, brine and dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex: ethyl acetate 4:1→CH2Cl2: hex 1:1) to give the title compound as an off white solid.

Workup

  1. waitat 0° C. for 5 hours
  2. customuntil all the starting material is consumed
  3. customquenched with ice
  4. extractionextracted with EtOAc (30 ml×3)
  5. washthe combined organic layer was washed carefully with sat NaHCO3, brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by flash chromatography on a silica gel column (hex: ethyl acetate 4:1→CH2Cl2: hex 1:1)

Sources & evidence

ORD record
ord-feaa9e7c8c594ff9a4772093f81d1956
Source dataset
uspto-grants-2014_11
Patent number
US08889724B2

Reaction notes

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