Iodine → 3-Iodo-5-nitrobenzoic acid

HRID 418376Notes

Reaction equation

HRID 418376 reaction equation
[I:1]I.[N+:3]([C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=[O:10])([O-:5])=[O:4]>S(=O)(=O)(O)O>[I:1][C:13]1[CH:12]=[C:8]([CH:7]=[C:6]([N+:3]([O-:5])=[O:4])[CH:14]=1)[C:9]([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 807IodineHCID 84973-Nitrobenzoic acid

Product 1

HCID 805803-Iodo-5-nitrobenzoic acidYield 97,987.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of iodine (137.95 g, 0.5436 mmol) in fuming sulfuric acid (250 ml) was added m-nitrobenzoic acid (64.6 g, 0.3866 mmol) at room temperature. The reaction mixture was slowly heated to 85° C. overs 2 hours and stirred at the same temperature for another 12 hours. The reaction mixture was cooled to room temperature and poured into ice, and the aqueous solution was extracted with dichloromethane. The organic phase was separated and washed with water, 2.0 M solution of Na2S2O3 and brine, and then dried over Na2SO4. Solvent was removed under reduced pressure to yield 3-iodo-5-nitrobenzoic acid as slight yellow solid 111 g, yield 98%. MS (M+H)=294.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. additionpoured into ice
  3. extractionthe aqueous solution was extracted with dichloromethane
  4. customThe organic phase was separated
  5. washwashed with water, 2.0 M solution of Na2S2O3 and brine
  6. dry with materialdried over Na2SO4
  7. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f695a67ba7954dfaaaf1aae82e63a03d
Source dataset
uspto-grants-2012_01
Patent number
US08093275B2

Reaction notes

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