HCID 90455890, compound → 4-Chloro-5-iodo-2-methoxyaniline

HRID 588774Notes

Reaction equation

HRID 588774 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([N+:10]([O-])=O)=[CH:4][C:3]=1[I:13]>C(O)(=O)C.O.[Fe]>[Cl:1][C:2]1[C:3]([I:13])=[CH:4][C:5]([NH2:10])=[C:6]([O:8][CH3:9])[CH:7]=1

Participants

5

Reactant 1

HCID 90455890HCID 90455890, compound

Product 1

HCID 917583774-Chloro-5-iodo-2-methoxyanilineYield 85%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-chloro-2-iodo-5-methoxy-4-nitrobenzene (113 g, 0.361 mol) in acetic acid (1 L) and water (50 mL) at 50° C., Fe (50.5 g, 0.903 mol) was added and the resulting mixture was stirred at 50° C. for 2 h. The mixture was allowed to cool to room temperature and then poured into ice-water. The precipitate was collected by filtration and rinsed with water. This crude product was dissolved with ethyl acetate (1 L) and filtered. The filtrate was washed with saturated NaHCO3 solution and brine. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to afford the desired product (87 g, 85% yield).

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe precipitate was collected by filtration
  3. washrinsed with water
  4. dissolutionThis crude product was dissolved with ethyl acetate (1 L)
  5. filtrationfiltered
  6. washThe filtrate was washed with saturated NaHCO3 solution and brine
  7. dry with materialThe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3b40ab883a254c87ad142c9c418d6fe1
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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