Dimethylformamide → 2-(3-Fluoro-2-hydroxyphenyl)acetonitrile

HRID 1712396Notes

Reaction equation

HRID 1712396 reaction equation
[F:1][C:2]1[C:7](CO)=[CH:6][CH:5]=[CH:4][C:3]=1[OH:10].[C-:11]#N.[Na+].C[N:15]([CH3:18])C=O>O>[F:1][C:2]1[C:3]([OH:10])=[C:4]([CH2:11][C:18]#[N:15])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 224461882-Fluoro-3-(hydroxymethyl)phenol

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4.89 g of 2-fluoro-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 (cautionl 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 (cautionl 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-fdfafa95938d4259bf062e630c068ea4
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Reaction notes

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