1-Octanol → HCID 18958547, compound

HRID 2406027Notes

Reaction equation

HRID 2406027 reaction equation
[CH2:1]([OH:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[H-].[Na+].[Br:12][C:13]1[CH:14]=[CH:15][C:16](F)=[C:17]([CH:20]=1)[C:18]#[N:19].O>CN(C)C=O>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[C:17]([CH:20]=1)[C:18]#[N:19]

Participants

6

Reactant 4

HCID 9571-OctanolHCID 962WaterHCID 24758Sodium hydrideHCID 27249005-Bromo-2-fluorobenzonitrile

Product 1

HCID 18958547HCID 18958547, compoundYield 105%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Octanol (0.834 g) was dissolved in N,N-dimethylformamide (10 ml), and sodium hydride (60%, 0.256 g) was added. After stirring for 30 min, 5-bromo-2-fluorobenzonitrile (0.640 g) was added, and the mixture was further stirred at 40-50° C. for 1 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give the object product (1.042 g) as a colorless oil.

Workup

  1. stirringthe mixture was further stirred at 40-50° C. for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2304dfdf6d874875977c9b036875c93f
Source dataset
uspto-grants-2014_08
Patent number
US08809304B2

Reaction notes

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