Water → HCID 20987598, compound

HRID 1093306Notes

Reaction equation

HRID 1093306 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[Br:13][C:14]1[CH:15]=[CH:16][C:17](F)=[C:18]([CH:21]=1)[C:19]#[N:20].O>CN(C)C=O>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([O:10][CH2:9][CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:18]([CH:21]=1)[C:19]#[N:20]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 31234BenzenepropanolHCID 27249005-Bromo-2-fluorobenzonitrile

Product 1

HCID 20987598HCID 20987598, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Phenylpropanol (2.17 g) was dissolved in N,N-dimethylformamide (32 ml), and sodium hydride (60%, 0.638 g) was added at room temperature. After stirring for 1 hr, 5-bromo-2-fluorobenzonitrile (1.60 g) was added, and the mixture was further stirred at 40-50° C. for 3 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. The residue was purified by silica gel column chromatography to give the object product (2.30 g) as a colorless oil.

Workup

  1. stirringthe mixture was further stirred at 40-50° C. for 3 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-48b96ecdec3f418abe65162a11ce06a2
Source dataset
uspto-grants-2012_03
Patent number
US08129361B2

Reaction notes

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