Water → HCID 50993163, compound

HRID 1847951Notes

Reaction equation

HRID 1847951 reaction equation
[CH3:1][CH:2]([CH3:5])[CH2:3][OH:4].[H-].[Na+].F[C:9]1[CH:16]=[CH:15][C:14]([I:17])=[CH:13][C:10]=1[C:11]#[N:12].O>CN(C)C=O>[I:17][C:14]1[CH:15]=[CH:16][C:9]([O:4][CH2:3][CH:2]([CH3:5])[CH3:1])=[C:10]([CH:13]=1)[C:11]#[N:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6560IsobutanolHCID 24758Sodium hydrideHCID 27789282-Fluoro-5-iodobenzonitrile

Product 1

HCID 50993163HCID 50993163, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-methyl-1-propanol (0.56 mL, 6.06 mmol) in N,N-dimethylformamide (10 mL) was cooled to 0° C. and to this was added sodium hydride (242 mg, a 60% suspension in mineral oil, 6.06 mmol) in small portions. The turbid reaction mixture was stirred at 0° C. for 5 minutes and the temperature was raised to 23° C. Thereafter, the mixture was stirred at room temperature for 10 minutes and cooled again to 0° C. To the reaction mixture was added 2-fluoro-5-iodobenzonitrile (1.0 g, 4.04 mmol) and, after being warmed to room temperature, the reaction mixture was stirred for 1.5 hours. After the reaction was complete, water (20 mL) was added to the reaction mixture, which was extracted with ethyl acetate (3×30 mL). The organic phases were combined, washed with a saturated aqueous sodium chloride solution (3×30 mL), and thereafter dried over anhydrous magnesium sulfate. After removing magnesium sulfate by filtration, the solvent was concentrated under reduced pressure. The crude product obtained was purified by silica gel chromatography (hexane/ethyl acetate=98/2) to obtain the title compound (950 mg). Yield, 78%.

Workup

  1. customThe turbid reaction mixture
  2. temperaturethe temperature was raised to 23° C
  3. stirringThereafter, the mixture was stirred at room temperature for 10 minutes
  4. temperaturecooled again to 0° C
  5. temperatureafter being warmed to room temperature
  6. stirringthe reaction mixture was stirred for 1.5 hours
  7. extractionwas extracted with ethyl acetate (3×30 mL)
  8. washwashed with a saturated aqueous sodium chloride solution (3×30 mL)
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customAfter removing magnesium sulfate
  11. filtrationby filtration
  12. concentrationthe solvent was concentrated under reduced pressure
  13. customThe crude product obtained
  14. customwas purified by silica gel chromatography (hexane/ethyl acetate=98/2)

Sources & evidence

ORD record
ord-18c93e41a7594a27af3ce4e52e56ac9a
Source dataset
uspto-grants-2015_02
Patent number
US08952174B2

Reaction notes

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