Iodine → 1,3-Dimethyl-5-iodo-2-nitrobenzene

HRID 1662278Notes

Reaction equation

HRID 1662278 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N+:9]([O-:11])=[O:10].OS(O)(=O)=O.II.[I:19](O)(=O)(=O)=O>O.C(O)(=O)C>[I:19][C:6]1[CH:5]=[C:4]([CH3:8])[C:3]([N+:9]([O-:11])=[O:10])=[C:2]([CH3:1])[CH:7]=1

Participants

7

Reactant 4

HCID 807IodineHCID 1118Sulfuric AcidHCID 66722,6-DimethylnitrobenzeneHCID 65185Metaperiodic acid

Product 1

HCID 113119441,3-Dimethyl-5-iodo-2-nitrobenzeneYield 88.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 2,6-dimethylnitrobenzene (151 g, 1.0 mol), acetic acid (1200 ml), and conc. H2SO4 (60 ml) was added iodine (102 g, 0.4 mol) and periodic acid dehydrate (205 g, 0.9 mol). The resulting solution was heated at 90° C. for 4 days. After cooling to room temperature, the reaction mixture was diluted with water (2000 ml). The yellow crystals were filtered and washed with water to give 220 g of pure product (79%). 1H-NMR δ (DMSO-d6, 300 MHz): 7.95 (d, J=7.8 Hz, 1H), 7.08 (d, J=7.8 Hz, 1H), 2.27 (s, 3H), 2.16 (s, 3H).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationThe yellow crystals were filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-9479ae65211048f9afb4186c4834d64e
Source dataset
uspto-grants-2011_10
Patent number
US08030518B2

Reaction notes

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