Boron tribromide → 2-(3-Hydroxyphenyl)acetonitrile

HRID 337244Notes

Reaction equation

HRID 337244 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]#[N:11])[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][C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 88310(3-Methoxyphenyl)acetonitrile

Product 1

HCID 137810422-(3-Hydroxyphenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(3-Methoxyphenyl)acetonitrile (3.6 g, 25.4 mmol) in dry methylene chloride (20 ml) was added BBr3 (55 ml, 1M in CH2Cl2, 55 mmol) at −78° C. under argon atmosphere. The reaction mixture was warmed to ambient temperature for 48 hours, quenched by crushed ice, and extracted with methylene chloride. The organic layer was dried over Na2SO4, filtered, concentrated and purified by flash chromatography on a silica gel column (CH2Cl2: ethyl acetate 4:1) to give the title compound as oil.

Workup

  1. customquenched
  2. customby crushed ice
  3. extractionextracted with methylene chloride
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash chromatography on a silica gel column (CH2Cl2: ethyl acetate 4:1)

Sources & evidence

ORD record
ord-6d19e095ba264afdb9c2b489b3d3dfdb
Source dataset
uspto-grants-2014_11
Patent number
US08889724B2

Reaction notes

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