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

HRID 2255177Notes

Reaction equation

HRID 2255177 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 93%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To 100 g (0.64 mol) of 5-fluoro-2-nitrophenol in 1000 ml of methyl ethyl ketone were added 105 g (0.76 mol) K2CO3 (freshly ground) followed by 107 g (0.70 mol) of methyl bromoacetate. The reaction mixture was refluxed for 6 hours then cooled to room temperature and stirred for an additional 18 hours. The reaction mixture was poured into 1 L of water, the phases were separated, and the aqueous phase was extracted with EtOAc (2×600 ml). The combined organics were then dried (Na2SO4) and concentrated in vacuo to give 135 g (93% yield) of the desired product as a yellow solid, m.p. 85°-57° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 6 hours
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted with EtOAc (2×600 ml)
  4. dry with materialThe combined organics were then dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4fe6f0eb37064445a4acd1f1723b649d
Source dataset
uspto-grants-1993_08
Patent number
US05238908

Reaction notes

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