Water → 5-Bromo-2-[3-(3-methylphenyl)propoxy]benzonitrile

HRID 1093515Notes

Reaction equation

HRID 1093515 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][OH:11])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[Br:14][C:15]1[CH:16]=[CH:17][C:18](F)=[C:19]([CH:22]=1)[C:20]#[N:21].O>CN(C)C=O>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([O:11][CH2:10][CH2:9][CH2:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=2)=[C:19]([CH:22]=1)[C:20]#[N:21]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27249005-Bromo-2-fluorobenzonitrileHCID 102612513-(3-Methylphenyl)propan-1-ol

Product 1

HCID 594075275-Bromo-2-[3-(3-methylphenyl)propoxy]benzonitrileYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 15-1 (1.30 g) was dissolved in N,N-dimethylformamide (30 ml) and sodium hydride (60%, 1.04 g) was added at room temperature. After stirring for 30 min, 5-bromo-2-fluorobenzonitrile (1.00 g) was added, and the mixture was stirred at 50° C. for 4 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the object product (1.04 g) as a yellow oil.

Workup

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

Sources & evidence

ORD record
ord-3f25478d4ec64dac8fa6f8e0ae338c19
Source dataset
uspto-grants-2012_03
Patent number
US08129361B2

Reaction notes

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