Iodine → 3-Iodo-4-methyl-5-nitrobenzoic acid

HRID 446220

Reaction equation

HRID 446220 reaction equation
[I:1]I.[CH3:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=1[N+:13]([O-:15])=[O:14]>S(=O)(=O)(O)O>[I:1][C:12]1[CH:11]=[C:7]([CH:6]=[C:5]([N+:13]([O-:15])=[O:14])[C:4]=1[CH3:3])[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 807IodineHCID 73194-Methyl-3-nitrobenzoic acid

Product 1

HCID 596277773-Iodo-4-methyl-5-nitrobenzoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of iodine (19.6 g, 77.3 mmol) in fuming sulfuric acid (35 mL) was added 4-methyl-3-nitro-benzoic acid (10.0 g, 55.2 mmol). The mixture was stirred at 85° C. over night, then cooled to room temperature and poured over ice. The mixture was partitioned between ethyl acetate and aqueous sodium bisulfite, and the organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure to give 16.06 g (95%) of 3-iodo-4-methyl-5-nitro-benzoic acid.

Workup

  1. temperaturecooled to room temperature
  2. additionpoured over ice
  3. customThe mixture was partitioned between ethyl acetate and aqueous sodium bisulfite
  4. customthe organic layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0b8f3e28eb3d4330a914fec7f029f573
Source dataset
uspto-grants-2013_07
Patent number
US08476457B2

Linked notes

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