Potassium Carbonate → 1-Chloro-4-[(4-methoxybenzyl)oxy]-2-nitrobenzene

HRID 883857Notes

Reaction equation

HRID 883857 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].Cl[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 691274-Chloro-3-nitrophenolHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 106614161-Chloro-4-[(4-methoxybenzyl)oxy]-2-nitrobenzeneYield 96%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-chloro-3-nitro-phenol (0.5 g, 2.88 mmol), 1-chloromethyl-4-methoxy-benzene (0.496 g, 3.17 mmol), potassium carbonate (1.19 g, 8.64 mmol) and tetrabutylammonium iodide (0.005 g, 0.0135 mmol) in N,N-dimethylformamide (5 ml) was stirred at room temperature for 16 hours. Afterwards ice water (10 mL) was added to the solution and the resultant solid was collected by filtration and dried in a vacuum oven to provide the title compound (0.812 g, 96%).

Workup

  1. filtrationthe resultant solid was collected by filtration
  2. customdried in a vacuum oven

Sources & evidence

ORD record
ord-0d4b4774943d432698cd416fd1a1756c
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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