4-Nitrophenol → 4-Chloro-6-(4-nitrophenoxy)pyrimidine

HRID 2200092Notes

Reaction equation

HRID 2200092 reaction equation
[OH-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)([O-:5])=[O:4].[Cl:13][C:14]1[CH:19]=[C:18](Cl)[N:17]=[CH:16][N:15]=1>O.CC(C)=O>[Cl:13][C:14]1[CH:19]=[C:18]([O:12][C:9]2[CH:10]=[CH:11][C:6]([N+:3]([O-:5])=[O:4])=[CH:7][CH:8]=2)[N:17]=[CH:16][N:15]=1

Participants

6

Reactant 3

HCID 9804-NitrophenolHCID 14798Sodium HydroxideHCID 709434,6-Dichloropyrimidine

Product 1

HCID 143638504-Chloro-6-(4-nitrophenoxy)pyrimidineYield 99.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Dissolve NaOH (2.8 g, 71.9 mmol) in water (90 mL) at 0° C. Add para-nitrophenol (10 g, 71.9 mmol), and then a solution of 4,6-dichloropyrimidine (10.7 g, 71.9 mmol) in acetone (90 mL). Stir the reaction at 70° C. for 24 hrs. Cool the reaction, collect the solid, rinse the solid with the mixture of acetone-water (1:1, 20 mL), and dry the solid to afford the title compound (18 g, 77.8%). MS: (M+Na): 274.0.

Workup

  1. customthe reaction at 70° C. for 24 hrs
  2. temperatureCool
  3. customthe reaction
  4. customcollect the solid
  5. washrinse the solid
  6. additionwith the mixture of acetone-water (1:1, 20 mL)
  7. customdry the solid

Sources & evidence

ORD record
ord-a03660c8dc4c48b683ff233f662c80d2
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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