1-Chloro-4-(chloromethyl)benzene → 2-Chloro-1-(4-chlorobenzyloxy)-4-(1-pyrazolyl)methylbenzene

HRID 2292656Notes

Reaction equation

HRID 2292656 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:13]=[C:12]([CH2:14][N:15]2[CH:19]=[CH:18][CH:17]=[N:16]2)[CH:11]=[CH:10][C:9]=1[OH:20].[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1.[Cl-].[NH4+]>CN(C)C=O>[Cl:7][C:8]1[CH:13]=[C:12]([CH2:14][N:15]2[CH:19]=[CH:18][CH:17]=[N:16]2)[CH:11]=[CH:10][C:9]=1[O:20][CH2:26][C:25]1[CH:28]=[CH:29][C:22]([Cl:21])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 21833668HCID 21833668, compound

Product 1

HCID 214789842-Chloro-1-(4-chlorobenzyloxy)-4-(1-pyrazolyl)methylbenzeneYield 94.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of potassium carbonate (298 mg), 2-chloro-4-(1-pyrazolyl)methylphenol (300 mg) and anhydrous N,N-dimethylformamide (200 ml) was added dropwise an anhydrous N,N-dimethylformamide solution (2 ml) of 4-chlorobenzyl chloride (232 mg) at room temperature under stirring. This mixture was then stirred at the same temperature for 12 hours, and poured into ice-cooled saturated aqueous ammonium chloride solution, which was extracted with ethyl acetate. The organic layer was washed with water and then saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, which afforded 454 mg of 2-chloro-1-(4-chlorobenzyloxy)-4-(1-pyrazolyl)methylbenzene (compound 4). Yield, 95%.

Workup

  1. stirringThis mixture was then stirred at the same temperature for 12 hours
  2. additionpoured into ice-
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialsaturated sodium chloride solution, dried with anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8b1ffe8ee64540d280fac5c0c064cc71
Source dataset
uspto-grants-1997_11
Patent number
US05684022

Reaction notes

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