Water → 2,4'-Dichloro-4-nitrodiphenyl ether

HRID 2197812Notes

Reaction equation

HRID 2197812 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[Cl:11].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Cl:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[O:19][C:16]1[CH:17]=[CH:18][C:13]([Cl:12])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 46844-ChlorophenolHCID 74431,2-Dichloro-4-nitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 897512,4'-Dichloro-4-nitrodiphenyl etherYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1,2-dichloro-4-nitro-benzene (9.2 g, 48 mmol), 4-chloro-phenol (6.2 g, 48 mmol) and potassium carbonate (19.9 g, 144 mmol) in DMF (80 mL) was heated to 90° C. for 16 hours. After cooling to room temperature the mixture was poured into water (600 mL) and extracted with ethyl acetate. The combined extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated under vacuum to provide the title compound (13.5 g, 99%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-75898dc56cef4db88a66cff87685412f
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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