1-Chloro-4-nitrobenzene → 1-Chloro-2-iodo-4-nitrobenzene

HRID 1038007Notes

Reaction equation

HRID 1038007 reaction equation
[I:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1>FC(F)(F)S(O)(=O)=O>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[I:1]

Participants

4

Reactant 2

HCID 74741-Chloro-4-nitrobenzeneHCID 120273N-Iodosuccinimide

Product 1

HCID 3127141-Chloro-2-iodo-4-nitrobenzeneYield 62%

Reagents, catalysts & solvents 1

HCID 62406Trifluoromethanesulfonic acidSolvent

Procedure

N-Iodosuccinimide (1.71 g, 7.60 mmol) was added to a solution of 1-chloro-4-nitrobenzene (1.17 g, 7.42 mmol) in trifluoromethanesulfonic acid (10 ml) at 0° C., then stirred 1 hour at room temperature. The reaction was quenched with ice-water and extracted with MeCl2 (3×50 ml). Organics were combined washed with 10% sodium bisulfite (20 ml) then dried over Na2SO4, filtered and evaporated solvent yielding the title compound as a white solid (1.3 g, 62%).

Workup

  1. customThe reaction was quenched with ice-water
  2. extractionextracted with MeCl2 (3×50 ml)
  3. washOrganics were combined washed with 10% sodium bisulfite (20 ml)
  4. dry with materialthen dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated solvent

Sources & evidence

ORD record
ord-336b2a2815fa423f8160a2482b11fa5d
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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