Water → 4-(Benzyloxy)-2-fluorobenzonitrile

HRID 2080119Notes

Reaction equation

HRID 2080119 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:10])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CN(C)C=O.C(OCC)(=O)C>[CH2:17]([O:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:10])[CH:3]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27346752-Fluoro-4-hydroxybenzonitrile

Product 1

HCID 113336284-(Benzyloxy)-2-fluorobenzonitrileYield 92%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-hydroxy-2-fluoro-benzonitrile (1.0 g, 7.3 mmol) in N,N-dimethylformamide (15 mL) was added potassium carbonate (2.09, 15 mmol) and benzyl bromide (0.87 mL, 7.3 mmol), and the solution was stirred at room temperature for 5 hours. Water and ethyl acetate were added to the reaction solution, which was then extracted, washed with brine, then, the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1), and the title compound (1.5 g, 6.7 mmol, 92%) was obtained as a white solid.

Workup

  1. extractionwas then extracted
  2. washwashed with brine
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-49bc30ba1b004c77b80053f444d14fea
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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