Boron tribromide → 3-(3-Hydroxyphenyl)propanenitrile

HRID 337254Notes

Reaction equation

HRID 337254 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]#[N:12])[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]#[N:12])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 100348983-(3-Methoxyphenyl)propanenitrile

Product 1

HCID 17123123-(3-Hydroxyphenyl)propanenitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-(3-methoxyphenyl)propanenitrile (Step A, 1.71 g, 10.6 mmol) in dry CH2Cl2 (20 ml) was added BBr3 (1M in CH2Cl2, 5.32 g, 21.2 mmol) at −78° C. under argon. The reaction mixture was stirred at the same temperature for 2 hours and then at 0° C. for 4 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 2:1) to give the title compound.

Workup

  1. waitat 0° C. for 4 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 2:1)

Sources & evidence

ORD record
ord-9f6363b7f4b2411586f959cc81700f97
Source dataset
uspto-grants-2014_11
Patent number
US08889724B2

Reaction notes

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