Water → 2-(3-Hydroxyphenyl)acetonitrile

HRID 62591

Reaction equation

HRID 62591 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>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

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 DCM) cooled at 0° C. under nitrogen 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 DCM, washed with brine and dried over anhydrous Na2SO4. After evaporation, the crude mixture is chromatographed on silica gel using PE/EtAc (80/20) as an eluant, yielding 1.28 g (71%) of 2-(3-hydroxyphenyl)acetonitrile.

Workup

  1. additionis added
  2. extractionthe organic phase is extracted three times with DCM
  3. washwashed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customAfter evaporation
  6. customthe crude mixture is chromatographed on silica gel using PE/EtAc (80/20) as an eluant

Sources & evidence

ORD record
ord-76355798d6a14caaba26e77622c23f49
Source dataset
uspto-grants-2016_09
Patent number
US09447029B2

Linked notes

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