Water → Methyl 2-(5-fluoro-2-nitrophenoxy)acetate

HRID 2255182Notes

Reaction equation

HRID 2255182 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]([O:22][CH3:23])=[O:21].O>C(C(C)=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:7]=1)[O:8][CH2:19][C:20]([O:22][CH3:23])=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 99375-Fluoro-2-nitrophenolHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate

Product 1

HCID 2779697Methyl 2-(5-fluoro-2-nitrophenoxy)acetateYield 91.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To 10 g (63.7 mmol) of 5-fluoro-2-nitrophenol in 100 ml of methyl ethyl ketone was added 10.5 g (76.4 mmol) of finely ground potassium carbonate followed by 10.7 g (70.1 mmol) of methyl bromoacetate. The resulting suspension was refluxed for 6 hours and then stirred at room temperature overnight. During this time it went from a deep red color to pale yellow. The reaction was poured into one liter of water, the layers were separated and the aqueous layer was extracted twice more with EtOAc (2×100 ml). The organics were combined, dried (Na2SO4), filtered and evaporated to dryness in vacuo to give 13.3 g (91% yield) of methyl 5-fluoro-2-nitrophenoxyacetate as a light yellow solid (m.p. 85°-87° C.).

Workup

  1. temperatureThe resulting suspension was refluxed for 6 hours
  2. customthe layers were separated
  3. extractionthe aqueous layer was extracted twice more with EtOAc (2×100 ml)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-4a5c17da86f3490c9bb2575debbe8a05
Source dataset
uspto-grants-1993_08
Patent number
US05238908

Reaction notes

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