Water → HCID 57704521, compound

HRID 2406021Notes

Reaction equation

HRID 2406021 reaction equation
[CH2:1]([OH:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[H-].[Na+].[Br:11][C:12]1[CH:13]=[CH:14][C:15](F)=[C:16]([CH:19]=1)[C:17]#[N:18].O>CN(C)C=O>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([O:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[C:16]([CH:19]=1)[C:17]#[N:18]

Participants

6

Reactant 4

HCID 962WaterHCID 8129HeptanolHCID 24758Sodium hydrideHCID 27249005-Bromo-2-fluorobenzonitrile

Product 1

HCID 57704521HCID 57704521, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Heptanol (1.55 g) was dissolved in N,N-dimethylformamide (24 ml), and sodium hydride (0.321 g) was added at room temperature. The mixture was stirred for 1 hr, 5-bromo-2-fluorobenzonitrile (2.43 g) was added, and the mixture was further stirred for 50 min. The reaction mixture was poured into water, extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. To consume the starting material, 5-bromo-2-fluorobenzonitrile, the reaction was performed again under the same conditions, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1-5:1) to give the object product (3.10 g) as a colorless oil.

Workup

  1. stirringthe mixture was further stirred for 50 min
  2. extractionextracted 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. customTo consume the starting material, 5-bromo-2-fluorobenzonitrile
  7. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1-5:1)

Sources & evidence

ORD record
ord-fe554f29785243fcb9acf182995c314d
Source dataset
uspto-grants-2014_08
Patent number
US08809304B2

Reaction notes

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