Potassium Hydroxide → HCID 18625320, compound

HRID 1859398Notes

Reaction equation

HRID 1859398 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12].[OH-].[K+].Cl[CH:16]([CH3:21])[C:17]([O:19][CH3:20])=[O:18]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[O:12][CH:16]([CH3:21])[C:17]([O:19][CH3:20])=[O:18]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 28659Methyl 2-chloropropionateHCID 158655Phenol, 2-chloro-4-fluoro-5-nitro-

Product 1

HCID 18625320HCID 18625320, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At 22° C., 100 g (0.522 mol) of 2-chloro-4-fluoro-5-nitrophenol were added with stirring to a solution of 34.5 g (0.522 mol) of 85% strength potassium hydroxide in 500 ml of methanol, and the mixture was stirred for another 30 min. At 40° C., the reaction mixture was then concentrated under reduced pressure. The residue was dried at 50° C. in a vacuum cabinet overnight. The pulverulent residue was then, at 40° C., dissolved with stirring in 1 l of dimethylformamide (DMF), 70.7 g (0.574 mol) of methyl 2-chloropropionate were added dropwise at 50° C. over a period of 30 min and the mixture was stirred at 80° C. for another 2 h. The solvent was removed under reduced pressure, the residue was introduced into 700 ml of water and undissolved components were filtered off. The aqueous phase was extracted three times with in each case 300 ml of methyl tert-butyl ether. The combined organic extracts were washed with about 500 ml of saturated sodium chloride solution and dried over magnesium sulfate. Concentration gave 106 g (73.1% of theory) of the title compound as a colorless resin.

Workup

  1. concentrationAt 40° C., the reaction mixture was then concentrated under reduced pressure
  2. customThe residue was dried at 50° C. in a vacuum cabinet overnight
  3. dissolutionat 40° C., dissolved
  4. stirringwith stirring in 1 l of dimethylformamide (DMF)
  5. stirringthe mixture was stirred at 80° C. for another 2 h
  6. customThe solvent was removed under reduced pressure
  7. additionthe residue was introduced into 700 ml of water and undissolved components
  8. filtrationwere filtered off
  9. extractionThe aqueous phase was extracted three times with in each case 300 ml of methyl tert-butyl ether
  10. washThe combined organic extracts were washed with about 500 ml of saturated sodium chloride solution
  11. dry with materialdried over magnesium sulfate
  12. concentrationConcentration

Sources & evidence

ORD record
ord-3c1ba73bd8754d61b275e0d3f2ee11d8
Source dataset
uspto-grants-2003_03
Patent number
US06528455B1

Reaction notes

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