2-Chloro-4-fluoro-5-nitrophenyl methyl carbonate → 2-Fluoro-5-methoxycarbonyloxyaniline

HRID 1596242Notes

Reaction equation

HRID 1596242 reaction equation
Cl[C:2]1[C:7]([O:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][C:5]([N+:13]([O-])=O)=[C:4]([F:16])[CH:3]=1>[Pd].C(O)C>[F:16][C:4]1[CH:3]=[CH:2][C:7]([O:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][C:5]=1[NH2:13]

Participants

4

Reactant 1

HCID 37866902-Chloro-4-fluoro-5-nitrophenyl methyl carbonate

Product 1

HCID 217015692-Fluoro-5-methoxycarbonyloxyanilineYield 47.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

4-Chloro-5-methoxycarbonyloxy-2-fluoronitrobenzene (1.2 g, 4.8 mmol), (as described in EP 61741 A2), and 10% palladium-on-charcoal catalyst (500 mg) in ethanol (100 ml) was stirred under hydrogen at 1 atmosphere pressure for 18 hours. A further batch of 10% palladium-on-charcoal catalyst (500 mg) was added and the mixture stirred under hydrogen for a further 3 hours. The catalyst was removed by filtration through diatomaceous earth and the solvent removed from the filtrate by evaporation. The residue was purified by flash chromatography eluting with methylene chloride/hexane (1/4) to give 2-fluoro-5-methoxycarbonyloxyaniline (0.42 g, 47%) as an oil.

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. customthe solvent removed from the filtrate by evaporation
  3. customThe residue was purified by flash chromatography
  4. washeluting with methylene chloride/hexane (1/4)

Sources & evidence

ORD record
ord-55875bb57cf048a29cbd970406e82197
Source dataset
uspto-grants-2001_09
Patent number
US06291455B1

Reaction notes

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