Bromobenzene → 2,4-Dimethoxy-N-phenylaniline

HRID 1982064Notes

Reaction equation

HRID 1982064 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1[O:13][CH3:14])(=O)[CH3:2].Br[C:16]1[CH:21]=CC=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[K+]>[Cu].II.C1(C)C=CC=CC=1.C(O)CC(C)C>[C:1]1([NH:4][C:5]2[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=2[O:13][CH3:14])[CH:18]=[CH:17][CH:16]=[CH:21][CH:2]=1

Participants

9

Reactant 4

HCID 7961BromobenzeneHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 89972Acetamide, N-(2,4-dimethoxyphenyl)-

Product 1

HCID 136437922,4-Dimethoxy-N-phenylanilineYield 58.2%

Reagents, catalysts & solvents 4

HCID 807IodineCatalystHCID 23978CopperCatalystHCID 1140TolueneSolventHCID 31260Isoamyl AlcoholSolvent

Procedure

To a mixture of 58.5 g of N-acetyl-2,4-dimethoxyaniline and 70.7 g of bromobenzene, 29 g of anhydrous potassium carbonate, 2.1 g of copper powder and 0.8 g of iodine were added and reacted at a temperature of from 170° to 180° C. for 20 hours. Then, to this reaction mixture, 30 g of potassium hydroxide and 100 ml of isoamyl alcohol were added and reacted at a temperature of from 120° to 130° C. for 3 hours. To this reaction mixture, 300 ml of toluene was added, and the toluene layer was separated by liquid separation, washed with water, concentrated and then purified by distillation under reduced pressure, whereby 40 g of oily N-phenyl-2,4-dimethoxyaniline was obtained. The boiling point of this product was from 161° to 164° C./2 mmHg.

Workup

  1. additionwere added
  2. customreacted at a temperature of from 170° to 180° C. for 20 hours
  3. customreacted at a temperature of from 120° to 130° C. for 3 hours
  4. customthe toluene layer was separated by liquid separation
  5. washwashed with water
  6. concentrationconcentrated
  7. distillationpurified by distillation under reduced pressure

Sources & evidence

ORD record
ord-1e629998b0de4e64930cc97179c5810d
Source dataset
uspto-grants-1986_06
Patent number
US04594601

Reaction notes

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