Trifluoromethanesulfonic anhydride → 1-Chloro-2-iodo-5-methoxy-4-nitrobenzene

HRID 588773Notes

Reaction equation

HRID 588773 reaction equation
FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.C1C(=O)N([I:23])C(=O)C1.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[C:27]([O:34][CH3:35])[CH:26]=1>OS(O)(=O)=O>[Cl:24][C:25]1[CH:26]=[C:27]([O:34][CH3:35])[C:28]([N+:31]([O-:33])=[O:32])=[CH:29][C:30]=1[I:23]

Participants

5

Reactant 3

HCID 67749Trifluoromethanesulfonic anhydrideHCID 811105-Chloro-2-nitroanisoleHCID 120273N-Iodosuccinimide2×

Product 1

HCID 904558901-Chloro-2-iodo-5-methoxy-4-nitrobenzeneYield 163.9%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of H2SO4 (600 mL, 90%), trifluoromethanesulfonic anhydride (11.3 g, 0.04 mol) and NIS (49.68 g, 0.22 mol) were added and resulting mixture was stirred at room temperature for 1 h. To this mixture, 4-chloro-2-methoxy-1-nitrobenzene (69 g, 0.368 mol) was added quickly. The mixture was stirred for 1 h, and then NIS (33.12 g, 0.148 mol) was slowly added to the mixture. The mixture was stirred at room temperature for 1 h and then was poured into ice-water. The precipitate collected by filtration, rinsed with water, aqueous NaSO3 and NaHCO3 solutions, and then dried in vacuo to afford the desired product (113 g, 98% yield).

Workup

  1. customresulting mixture
  2. stirringThe mixture was stirred for 1 h
  3. stirringThe mixture was stirred at room temperature for 1 h
  4. filtrationThe precipitate collected by filtration
  5. washrinsed with water, aqueous NaSO3 and NaHCO3 solutions
  6. customdried in vacuo

Sources & evidence

ORD record
ord-4d6b6fd4f5b945e6ba7266b07c205f78
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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