Sodium Cyanide → 2-(3-Fluoro-2-hydroxyphenyl)acetonitrile

HRID 1176378Notes

Reaction equation

HRID 1176378 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8]O)[C:3]=1[OH:10].[C-:11]#[N:12].[Na+]>CN(C)C=O.O>[F:1][C:2]1[C:3]([OH:10])=[C:4]([CH2:8][C:11]#[N:12])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 187554072-Fluoro-6-(hydroxymethyl)phenol

Product 1

HCID 684994132-(3-Fluoro-2-hydroxyphenyl)acetonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4.89 g of 2-fluoro-6-hydroxymethylphenol and 2.08 g of sodium cyanide in 120 ml of N,N-dimethylformamide is stirred at 120° C. over 24 hours. The reaction mixture is cooled, diluted with water and concentrated by evaporation. The residue is diluted with water and neutralized with conc. acetic acid (caution! hydrocyanic acid). The mixture is extracted with dichloromethane (3×). The combined organic phases are washed with water and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a violet solid from the residue by means of flash chromatography (SiO2 60F). Rf=0.32 (1:2 EtOAc-heptane); Rt=3.12.

Workup

  1. temperatureThe reaction mixture is cooled
  2. concentrationconcentrated by evaporation
  3. additionThe residue is diluted with water and neutralized with conc. acetic acid (caution! hydrocyanic acid)
  4. extractionThe mixture is extracted with dichloromethane (3×)
  5. washThe combined organic phases are washed with water and brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-1987e7beafb848b4a0afbc1d2dbac7db
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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