3,4-Dichlorophenol → HCID 68588944, compound

HRID 1496817Notes

Reaction equation

HRID 1496817 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl[C:11]1[C:16]([CH3:17])=[CH:15][C:14]([N+:18]([O-:20])=[O:19])=[C:13]([CH3:21])[CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[Cl:8])[O:9][C:11]1[C:16]([CH3:17])=[CH:15][C:14]([N+:18]([O-:20])=[O:19])=[C:13]([CH3:21])[CH:12]=1

Participants

5

Reactant 3

HCID 72583,4-DichlorophenolHCID 11430Potassium CarbonateHCID 2527931-Chloro-2,5-dimethyl-4-nitrobenzene

Product 1

HCID 68588944HCID 68588944, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

10.0 g (61.3 mmol) of 3,4-dichlorophenol, 10.4 g (55.8 mmol) of 4-chloro-2,5-dimethylnitrobenzene and 10.0 g (72.5 mmol) of potassium carbonate are stirred in 200 ml of N,N-dimethylformamide at 100° C. for 6 h, and the mixture is applied to ice, stirred at 0° C. for 15 min and then filtered. The solid is washed with water and hexane and dried under reduced pressure (18.0 g, 98.3% purity, 98.0% yield, log P (pH 2.3)=5.19).

Workup

  1. filtrationfiltered
  2. washThe solid is washed with water and hexane
  3. customdried under reduced pressure (18.0 g, 98.3% purity, 98.0% yield, log P (pH 2.3)=5.19)

Sources & evidence

ORD record
ord-247cd071ea3c4d399eb42567c48f0c51
Source dataset
uspto-grants-2015_12
Patent number
US09199922B2

Reaction notes

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