Methanol → HCID 68809527, compound

HRID 1782609Notes

Reaction equation

HRID 1782609 reaction equation
[H-].[Na+].[CH3:3][OH:4].F[C:6]1[C:13]([F:14])=[C:12]([I:15])[CH:11]=[CH:10][C:7]=1[C:8]#[N:9]>CN(C=O)C>[F:14][C:13]1[C:6]([O:4][CH3:3])=[C:7]([CH:10]=[CH:11][C:12]=1[I:15])[C:8]#[N:9]

Participants

5

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 688091892,3-Difluoro-4-iodobenzonitrile

Product 1

HCID 68809527HCID 68809527, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

Sodium hydride (60 mg, 2.5 mmol) was slurried in DMF (15 mL) and treated with dry methanol (120 μl, 96 mg, 3.0 mmol). After stirring for 10 minutes at 25° C., the solution was cooled to −25° C. and treated with 2,3-difluoro-4-iodobenzonitrile (500 mg, 1.9 mmol). After 25 minutes, the mixture was quenched by addition of 10% citric acid solution (5 mL) and warmed to 25° C. The mixture was extracted with ethyl ether (2×15 mL), the combined ether phases washed with water (5 mL), brine, dried (sodium sulfate) and evaporated to give 3-fluoro-4-iodo-2-methoxybenzonitrile (500 mg, 1.8 mmol): LC/MS (m/z=277).

Workup

  1. temperaturethe solution was cooled to −25° C.
  2. waitAfter 25 minutes
  3. customthe mixture was quenched by addition of 10% citric acid solution (5 mL)
  4. temperaturewarmed to 25° C
  5. extractionThe mixture was extracted with ethyl ether (2×15 mL)
  6. washthe combined ether phases washed with water (5 mL), brine
  7. dry with materialdried (sodium sulfate)
  8. customevaporated

Sources & evidence

ORD record
ord-029465e19df24386aaf7b22cb26ff2d0
Source dataset
uspto-grants-2009_03
Patent number
US07498468B2

Reaction notes

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