4-Chlorophenol → 1-Chloro-4-(4-nitrophenoxy)benzene

HRID 359070

Reaction equation

HRID 359070 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[N+:9]([C:12]1[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=1)([O-:11])=[O:10].C(=O)([O-])[O-].[K+].[K+]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:15]2[CH:16]=[CH:17][C:12]([N+:9]([O-:11])=[O:10])=[CH:13][CH:14]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 114661-Bromo-4-nitrobenzene

Product 1

HCID 157861-Chloro-4-(4-nitrophenoxy)benzeneYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

p-Chlorophenol (7 g), p-nitrobromobenzene (11.0 g) and potassium carbonate (9.02 g) in dimethylsufoxide (35 ml) were heated with stirring at 120° C. for 24 hours and cooled, and the mixture was poured into water. The resulting precipitate was collected by filtration and washed with water. The resultant was heated in a mixed solvent of methanol/water [4:1,(v/v)], and allowed to cool. The resulting product was collected by filtration to give 4-(4-chlorophenoxy)nitrobenzene (12.92 g).

Workup

  1. temperaturecooled
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. temperatureThe resultant was heated in a mixed solvent of methanol/water [4:1,(v/v)], and
  5. temperatureto cool
  6. filtrationThe resulting product was collected by filtration

Sources & evidence

ORD record
ord-abd26f5b9827450e90a5f585c85651fe
Source dataset
uspto-grants-1991_03
Patent number
US04999378

Linked notes

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