4-Bromophenol → 2-(4-Bromophenoxy)benzonitrile

HRID 51485

Reaction equation

HRID 51485 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[Br:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[C:4]#[N:5])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 678552-Fluorobenzonitrile

Product 1

HCID 227364352-(4-Bromophenoxy)benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-fluorobenzonitrile (28.8 g), 4-bromophenol (36.9 g), potassium carbonate (58.9 g) and dimethylformamide (30 ml) was heated with stirring under nitrogen at 120° C. for 5 hours. The mixture was allowed to stand overnight at ambient temperature and then partitioned between ethyl acetate and water. The organic layer was separated, washed, dried and evaporated to give an oil which solidified on standing. The solid was triturated with petroleum ether b.p. 40-60° C. and filtered to give 2-(4-bromophenoxy)benzonitrile.

Workup

  1. temperaturewas heated
  2. waitto stand overnight at ambient temperature
  3. custompartitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. washwashed
  6. customdried
  7. customevaporated
  8. customto give an oil which
  9. customThe solid was triturated with petroleum ether b.p. 40-60° C.
  10. filtrationfiltered

Sources & evidence

ORD record
ord-55b7fb0c0aa44265ba7561577d290abe
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Linked notes

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