Water → Methyl 4-amino-3-fluorobenzoate

HRID 428592Notes

Reaction equation

HRID 428592 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N+:12]([O-])=O)[C:5]([O:7][CH3:8])=[O:6].C(Cl)Cl.O>C(O)(=O)C.[Fe]>[NH2:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[F:1]

Participants

6

Reactant 3

HCID 962WaterHCID 6344DichloromethaneHCID 592761Methyl 3-fluoro-4-nitrobenzoate

Product 1

HCID 11182865Methyl 4-amino-3-fluorobenzoateYield 97%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of methyl 3-fluoro-4-nitrobenzoate(2.14 g, 10.8 mmol) and iron powder(2.63 g) in acetic acid(22 ml) was stirred at 50° C. for 2.5 h. After cooling down to room temperature, CH2Cl2(100 ml) and water(300 ml) was added to the mixture and filtered to remove iron powder. The organic layer was separated and the aqueous layer was extracted with CH2Cl2(70 mlx2). The CH2Cl2 solution was combined, washed with water, brine, dried(Na2SO4), and concentrated to give 1.77 g(97%) of pale brown solid.

Workup

  1. temperatureAfter cooling down to room temperature
  2. filtrationfiltered
  3. customto remove iron powder
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with CH2Cl2(70 mlx2)
  6. washwashed with water, brine, dried(Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b55b2207eb8b47cb8110fd461e30e37e
Source dataset
uspto-grants-2001_11
Patent number
US06313302B2

Reaction notes

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