Boron tribromide → 2-(3-Hydroxyphenyl)acetonitrile

HRID 1958839Notes

Reaction equation

HRID 1958839 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-964c2ef24c72429eba982a49e6dd90e4
Source dataset
uspto-grants-2013_04
Patent number
US08410154B2

Reaction notes

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