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

HRID 387981Notes

Reaction equation

HRID 387981 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1.[N+:9]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)([O-:11])=[O:10].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.CCCCCC.C(OCC)(=O)C.O>[Cl:8][C:6]1[CH:5]=[C:4]([O:18][C:15]2[CH:16]=[CH:17][C:12]([N+:9]([O-:11])=[O:10])=[CH:13][CH:14]=2)[N:3]=[CH:2][N:7]=1

Participants

8

Reactant 3

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 775312,4-Dichloropyrimidine

Product 1

HCID 143638504-Chloro-6-(4-nitrophenoxy)pyrimidineYield 77.5%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

2,4-Dichloropyrimidine (2.98 g, 20.0 mmol), 4-nitrophenol (2.78 g, 20.0 mmol) and potassium carbonate (4.15 g, 30.0 mmol) were stirred together in dimethylformamide (20 ml) at room temperature for 15 hours. The reaction solution was distributed between ethyl acetate and water, the organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (eluent-ethyl acetate:hexane=1:4), and the fraction containing the target substance was concentrated to obtain the title compound (3.89 g, 15.5 mmol, 77%) as colorless crystals.

Workup

  1. washthe organic layer was washed with water and saturated saline
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationthe drying agent was filtered off
  4. distillationthe filtrate was distilled off under reduced pressure
  5. customThe obtained crude product
  6. additionthe fraction containing the target substance
  7. concentrationwas concentrated

Sources & evidence

ORD record
ord-7e10958c2bbb40eba570bbfa7d9aa6c4
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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