Ethyl bromoacetate → Ethyl 2,3-dichloro-4-(4'-nitrophenoxy)phenoxyacetate

HRID 2166846Notes

Reaction equation

HRID 2166846 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[OH:19].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9][C:10]2[CH:11]=[CH:12][C:13]([N+:16]([O-:18])=[O:17])=[CH:14][CH:15]=2)[CH:5]=[CH:4][C:3]=1[O:19][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 13145676HCID 13145676, compound

Product 1

HCID 13145677Ethyl 2,3-dichloro-4-(4'-nitrophenoxy)phenoxyacetate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2,3-dichloro-4-(p-nitrophenoxy)phenol (11.5 g., 0.038 mole), ethyl bromoacetate (9.51 g., 0.057 mole) and pulverized potassium carbonate (7.9 g., 0.057 mole) in 100 ml. of 2-butanone was heated at reflux for 2 hours. The reaction mixture was then filtered and the filtrate concentrated under reduced pressure. The residue was taken into CH2Cl2 and the resulting solution was washed with aqueous NaCl and dried over MgSO4. Evaporation of the solvent was followed by trituration with hexane to furnish the solid product. Recrystallization from cyclohexane gave 12.5 g. of solid, m.p. 90°-91°.

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationThe reaction mixture was then filtered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. washthe resulting solution was washed with aqueous NaCl
  5. dry with materialdried over MgSO4
  6. customEvaporation of the solvent
  7. customto furnish the solid product
  8. customRecrystallization from cyclohexane
  9. customgave 12.5 g

Sources & evidence

ORD record
ord-cad16343c8ae43c081a2fe0ccad33cfa
Source dataset
uspto-grants-1983_06
Patent number
US04389416

Reaction notes

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