Sulfuric Acid → 1-Iodo-3-methyl-5-nitrobenzene

HRID 326647Notes

Reaction equation

HRID 326647 reaction equation
N[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([CH3:11])=[CH:4][C:3]=1[I:12].S(=O)(=O)(O)O.N([O-])=O.[Na+]>C(O)C>[I:12][C:3]1[CH:4]=[C:5]([CH3:11])[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[CH:2]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 197351992-Iodo-4-methyl-6-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 197352191-Iodo-3-methyl-5-nitrobenzeneYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-amino-3-iodo-5-nitrotoluene (14.0 g) in ethanol (70 ml) was added concentrated sulphuric acid (8 ml) dropwise, then the solution was heated to reflux and solid sodium nitrite (8.9 g) added in small amounts over 30 minutes. The mixture was refluxed a further one hour, and then was poured into ice water. The precipitate was washed with water and dried to yield 3-iodo-5-nitrotoluene (10.2 g). δ (360 MHz, DMSO-d6) 2.40 (3H, s, CH3), 8.07 (2H, bs, 2-H and 6-H) and 8.30 (1H, s, 4-H).

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux
  3. temperatureThe mixture was refluxed a further one hour
  4. washThe precipitate was washed with water
  5. customdried

Sources & evidence

ORD record
ord-1ffa6e4322d9405a9d7a215cb52ff09c
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Reaction notes

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