Methyl 2-(4-fluoro-3-nitrophenyl)acetate → HCID 22742091, compound

HRID 1264625Notes

Reaction equation

HRID 1264625 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][C:3]=1[N+:13]([O-])=O>CC(O)C.O.Cl.C(OCC)C.[Fe]>[NH2:13][C:3]1[CH:4]=[C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:7][C:2]=1[F:1]

Participants

7

Reactant 1

HCID 22742120Methyl 2-(4-fluoro-3-nitrophenyl)acetate

Product 1

HCID 22742091HCID 22742091, compoundYield 83.1%

Reagents, catalysts & solvents 5

HCID 313Hydrochloric AcidCatalystHCID 23925IronCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Procedure

Methyl 4-fluoro-3-nitrophenylacetate (5.0 g, 0.023 mol) and iron powder (3 g, 0.053 mol) were suspended in a mixture of propan-2-ol (50 ml) and water (5 ml). Concentrated hydrochloric acid (5 drops) was added at room temperature and the mixture was heated at reflux with stirring for 2 hours. The reaction mixture was cooled, diluted with diethyl ether, filtered through diatomaceous earth and the resulting filtrate was evaporated in vacuo. The residue was further purified by chromatography on silica gel, eluting with diethyl ether to yield methyl 3-amino-4-fluorophenylacetate (3.5 g) as a yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered through diatomaceous earth
  5. customthe resulting filtrate was evaporated in vacuo
  6. customThe residue was further purified by chromatography on silica gel
  7. washeluting with diethyl ether

Sources & evidence

ORD record
ord-1dba7b17adec4758907a97354fdb5e5a
Source dataset
uspto-grants-2003_04
Patent number
US06544989B2

Reaction notes

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