Dimethyl Sulfoxide → Ethyl 2-(3-fluoro-4-nitrophenyl)propanoate

HRID 2285804Notes

Reaction equation

HRID 2285804 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:11](C)([C:17](OCC)=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[Cl-].[Na+].CS(C)=O>O.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 5234Sodium ChlorideHCID 42638641,3-Diethyl 2-(3-fluoro-4-nitrophenyl)-2-methylpropanedioate

Product 1

HCID 12879863Ethyl 2-(3-fluoro-4-nitrophenyl)propanoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 100 millimoles of diethyl 2-(3-fluoro-4-nitrophenyl)-2-methylmalonate, 110 millimoles of sodium chloride and 50 milliliters of dimethyl sulfoxide is heated under nitrogen at about 130° to 180° C. for about 6 hours. On cooling the mixture is diluted with 100 milliliters of water and 100 milliliters of ethyl acetate. The layers are separated and the organic layer is washed two times with 24 milliliters of water. After drying over disodium sulfate the organic layer is concentrated in vacuo to give the desired ethyl 2-(3-fluoro-4-nitrophenyl)propionate.

Workup

  1. temperatureis heated under nitrogen at about 130° to 180° C. for about 6 hours
  2. temperatureOn cooling the mixture
  3. customThe layers are separated
  4. washthe organic layer is washed two times with 24 milliliters of water
  5. dry with materialAfter drying over disodium sulfate the organic layer
  6. concentrationis concentrated in vacuo

Sources & evidence

ORD record
ord-032a421ea8004774b9a045ccb28118a0
Source dataset
uspto-grants-1982_04
Patent number
US04324904

Reaction notes

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