Water → 2-(3-Hydroxyphenyl)acetonitrile

HRID 62596Notes

Reaction equation

HRID 62596 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.O>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 88310(3-Methoxyphenyl)acetonitrile

Product 1

HCID 137810422-(3-Hydroxyphenyl)acetonitrileYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(3-methoxyphenyl)acetonitrile (2 g; 13.59 mmol) in 13 mL of dry dichloromethane (DCM) cooled at 0° C. under an inert atmosphere, a 1M solution of BBr3 in DCM (28.54 mmol; 28.54 mL) is slowly added dropwise. The mixture is stirred at room temperature for 20 hours. The reaction mixture is then poured into ice, water is added and the organic phase is extracted three times with dichloromethane, washed with brine and dried over anhydrous Na2SO4. After evaporation, the crude mixture is purified by flash-chromatography on silica gel using petroleum ether/EtAc (80/20) as an eluant, affording 1.28 g (71%) of 2-(3-hydroxyphenyl)acetonitrile.

Workup

  1. additionis added
  2. extractionthe organic phase is extracted three times with dichloromethane
  3. washwashed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customAfter evaporation
  6. customthe crude mixture is purified by flash-chromatography on silica gel

Sources & evidence

ORD record
ord-421976812b0e42e5bece4cc9233e266c
Source dataset
uspto-grants-2016_09
Patent number
US09447029B2

Reaction notes

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