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

HRID 1993505Notes

Reaction equation

HRID 1993505 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[C:12]1[N:17]=[C:16]([Cl:18])[CH:15]=[CH:14][N:13]=1.[OH-].[Na+]>O.CC(C)=O>[Cl:18][C:16]1[CH:15]=[C:14]([O:10][C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[N:13]=[CH:12][N:17]=1

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 14798Sodium HydroxideHCID 775312,4-Dichloropyrimidine

Product 1

HCID 143638504-Chloro-6-(4-nitrophenoxy)pyrimidine

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Conditions

Temperature
62.5 °C

Procedure

4-Nitrophenol (2.8 g, 20.1 mmol), 2,4-dichloro-pyrimidine (3 g, 20.1 mmol), NaOH (0.8 g, 20.1 mmol) dissolved in H2O/acetone (80 ml; 1:1) are stirred at 60-65° C. for 1 h. The reaction solution is concentrated under reduced pressure and flash chromatographed (silica gel, 4.5×22 cm, AcOEt/hexane=1:4) to give the title compound of Stage 21.2 as a colorless solid: M+H=252/254; 1H-NMR (400 MHz, DMSO-d6): 8.67 (s, 1H, pyrimidinyl), 8.34 (d, 9 Hz, 2H, phenyl), 7.58 (d, 9 Hz, 2H, phenyl), 7.53 (s, 1H, pyrimidinyl); Rf (AcOEt/hexane=1:1): 0.16; m.p.=125.4-126.6° C.

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure and flash
  2. customchromatographed (silica gel, 4.5×22 cm, AcOEt/hexane=1:4)

Sources & evidence

ORD record
ord-0cb9536beeb6457884d6206da3f10f5b
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

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