Boron tribromide → 2-(3-Hydroxyphenyl)-2-methylpropanenitrile

HRID 516851Notes

Reaction equation

HRID 516851 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]([CH3:13])([CH3:12])[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]([C:9]([CH3:13])([CH3:12])[C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 101301932-(3-Methoxyphenyl)-2-methylpropanenitrile

Product 1

HCID 125381552-(3-Hydroxyphenyl)-2-methylpropanenitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(3-methoxyphenyl)-2-methylpropanenitrile (Step A, 4.5 g, 25.7 mmol) in methylene chloride (30 ml) was added BBr3 (1M in CH2Cl2, 50 ml) at −78° C. under argon, the cold bath was substituted by ice bath after 30 minutes and the reaction was stirred at the same temperature for 2 hours and then 30 minutes at room temperature. The reaction mixture was quenched by addition of ice and worked up by washing with water and brine. The organic layer was dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (methylene chloride:ethyl acetate, 5:1) to give the title compound.

Workup

  1. custom30 minutes
  2. customat room temperature
  3. customThe reaction mixture was quenched by addition of ice
  4. washby washing with water and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by flash chromatography on a silica gel column (methylene chloride:ethyl acetate, 5:1)

Sources & evidence

ORD record
ord-698197d5179b447fb450d83ef17af887
Source dataset
uspto-grants-2015_08
Patent number
US09115072B2

Reaction notes

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