1-Bromo-2-Chloroethane → 4-(2-Chloroethoxy)-2-methyl-1-nitrobenzene

HRID 1451636Notes

Reaction equation

HRID 1451636 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].Br[CH2:13][CH2:14][Cl:15].[OH-].[Na+]>O>[Cl:15][CH2:14][CH2:13][O:11][C:4]1[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([CH3:1])[CH:3]=1

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 14798Sodium HydroxideHCID 174123-Methyl-4-nitrophenol

Product 1

HCID 199746534-(2-Chloroethoxy)-2-methyl-1-nitrobenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 3-methyl-4-nitrophenol (10 g), 1-bromo-2-chloroethane (16 ml) and sodium hydroxide (2.9 g) in water (50 ml) was stirred under reflux for 16 h. The mixture was diluted with water and the product was extracted with methylene chloride. The organic extract was dried on sodium sulfate and concentrated in vacuo to give the title compound as an oil (10.81 g) NMR includes d 2.5 (s,3H,--CH3), 3.9 (t,2H,CH2 --O) and 4.3 (t,2H,--CH2 --Cl).

Workup

  1. temperatureunder reflux for 16 h
  2. extractionthe product was extracted with methylene chloride
  3. extractionThe organic extract
  4. customwas dried on sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0e44f407677b44bfb6a460fdcd54d422
Source dataset
uspto-grants-1997_02
Patent number
US05604237

Reaction notes

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