Methanol → HCID 68809527, compound

HRID 2249382Notes

Reaction equation

HRID 2249382 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-2a9398f053734df2b3b8e1a6a9968d7b
Source dataset
uspto-grants-2008_01
Patent number
US07314849B2

Reaction notes

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