Water → 4-(4-Chlorophenoxy)-3-nitropyridine

HRID 1642267Notes

Reaction equation

HRID 1642267 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23].O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2[N+:22]([O-:24])=[O:23])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 528401924-(4-Chlorophenoxy)-3-nitropyridineYield 88.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4-chlorophenol (1.00 g, 7.78 mmol) in DMF (5 ml) at room temperature was added potassium carbonate (2.15 g, 15.56 mmol) in DMF (10 mL) and the mixture was stirred at room temperature for 15 min. Then, 4-chloro-3-nitropyridine (1.23 g, 7.78 mmol) was added and the resulting solution was stirred at room temperature for 2 h. The mixture was poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried (MgSO4), filtered and evaporated. 4-(4-Chlorophenoxy)-3-nitropyridine (1.72 g, 88%) was obtained as a yellow solid, mp 93-94° C. (from EtOH), which was used in the next step without further purification.

Workup

  1. stirringthe resulting solution was stirred at room temperature for 2 h
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-51bcf476b6304bbca10c3bbed2f1caa4
Source dataset
uspto-grants-2012_02
Patent number
US08119627B2

Reaction notes

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