Sodium Iodide → HCID 10969971, compound

HRID 1768087Notes

Reaction equation

HRID 1768087 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([N+:17]([O-:19])=[O:18])=[CH:9][C:8]=1[N+:20]([O-:22])=[O:21])(=O)=O.[Na+].[I-:26]>CCOC(C)=O>[I:26][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([N+:17]([O-:19])=[O:18])=[CH:9][C:8]=1[N+:20]([O-:22])=[O:21]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 10915517HCID 10915517, compound

Product 1

HCID 10969971HCID 10969971, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (2) (5.0 g, 13.7 mmol) and NaI (7.0 g) in EtOAc (200 mL) was heated under reflux for 2 h. The mixture was cooled to room temperature and washed with sat. aq. Na2S2O3. The organic phase was dried, concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel. Elution with CH2Cl2, gave 1-iodo-2,4-dinitronaphthalene (3) (4.3 g 91%) as yellow needle: mp (EtOAc/CH2Cl2) 194–195° C.; 1H NMR [(CD3)2SO] δ 8.76 (s, 1H, H-3), 8.54 (m, 1H), 8.33 (m, 1H), 8.00(m, 2H); 13C NMR δ 151.81, 147.05, 134.97, 132.18, 131.24, 123.88, 123.26, 117.50, 102.66. Anal. (C10H5IN2O4) C, H, N.

Workup

  1. temperatureunder reflux for 2 h
  2. washwashed with sat. aq. Na2S2O3
  3. customThe organic phase was dried
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel
  6. washElution with CH2Cl2

Sources & evidence

ORD record
ord-9e49da773a8240518377d2cbac725190
Source dataset
uspto-grants-2007_06
Patent number
US07235578B2

Reaction notes

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