Dimethylformamide → 3,5-Difluoro-4-hydroxy-benzonitrile

HRID 2226649Notes

Reaction equation

HRID 2226649 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([OH:9])=[C:4]([F:10])[CH:3]=1.[Cu][C:12]#[N:13].CN(C)C=O>O>[F:10][C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([F:8])[C:5]=1[OH:9])[C:12]#[N:13]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 27362924-Bromo-2,6-difluorophenolHCID 178418546HCID 178418546, compound

Product 1

HCID 107494063,5-Difluoro-4-hydroxy-benzonitrileYield 35%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-bromo-2,6-difluorophenol (4.00 g, 19.0 mmol), copper (I) cyanide (1.72 g, 19.0 mmol), and dimethylformamide (40 mL) was refluxed for 6 hours, cooled to room temperature, diluted with water (150 mL), and filtered. The tan solids obtained were washed with water and retained. The combined filtrates were acidified (1N HCl) and extracted with ethyl acetate. The combined organic extracts were dried (MgSO4), concentrated in vacuo, and purified by flash chromatography (Silica Gel 60, 20% ethyl acetate in hexanes) to give 1.03 g of pure title compound as an off-white solid, mp 195°-197° C.

Workup

  1. temperaturewas refluxed for 6 hours
  2. filtrationfiltered
  3. customThe tan solids obtained
  4. washwere washed with water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. custompurified by flash chromatography (Silica Gel 60, 20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-fc6ff4d566ba45729e5b74b90e96a8fd
Source dataset
uspto-grants-1994_09
Patent number
US05349068

Reaction notes

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