Diiodomethane → 26516-42-7

HRID 456330

Reaction equation

HRID 456330 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:5]=1N)([O-:3])=[O:2].[I:14]CI>>[I:14][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:10][CH:9]=[CH:8][C:7]=1[N+:11]([O-:13])=[O:12]

Participants

3

Reactant 2

HCID 6346DiiodomethaneHCID 690702,6-Dinitroaniline

Product 1

HCID 1457118426516-42-7Yield 52%

Procedure

To a dispersion of 2,6-dinitroaniline (4.00 g, 0.021 mol) in diiodomethane (24 mL, 0.297 mol) isoamylnitrite (15 mL, 0.112 mol) was added (Smith et al., 1990, which is incorporated herein by reference). The mixture was stirred at room temperature for one hour, and then heated at 105° C. for eight hours. The excess of diiodomethane was removed in high vacuo. The residue was diluted with acetyl acetate (10 mL). Silica (ca 30 mL, mesh 230-400 Å) was added; the mixture was concentrated in vacuo and purified by column chromatography to yield 1-iodo-2,6-dinitrobenzene (3.21 g, 52%). 1H NMR (400 MHz, CDCl3): δ 7.84 (d, 2 H, J=8.0 Hz), 7.67 (t, 1 H, J=8.0 Hz).

Workup

  1. temperatureheated at 105° C. for eight hours
  2. customThe excess of diiodomethane was removed in high vacuo
  3. additionThe residue was diluted with acetyl acetate (10 mL)
  4. additionSilica (ca 30 mL, mesh 230-400 Å) was added
  5. concentrationthe mixture was concentrated in vacuo
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-10d042ef3af74fec831be2a65394c4db
Source dataset
uspto-grants-2013_07
Patent number
US08497360B2

Linked notes

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