Methanesulfonic Acid → Methyl 3,5-diiodobenzoate

HRID 1037512Notes

Reaction equation

HRID 1037512 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:11])[CH:10]=1)[C:5]([OH:7])=[O:6].[CH3:12]S(O)(=O)=O>CO>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:11])[CH:10]=1)[C:5]([O:7][CH3:12])=[O:6]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 985773,5-Diiodobenzoic acid

Product 1

HCID 53435545Methyl 3,5-diiodobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 3,5-diiodobenzoic acid (6.8 g, 18.18 mmol) in methanol (200.0 ml) was added CH3SO3H (0.5 ml). The reaction mixture was heated to reflux. After refluxing for 7.5 hours, most of the methanol was removed. Then, water (200.0 ml) was added and a dark-brown solid was collected by filtration. The product was purified by silica gel column chromatography using hexanes/ethyl acetate (8:2) as eluent. The final pure white product was obtained in the amount of 4.2 g (59.2%) by recrystallization from methanol/water:

Workup

  1. temperatureThe reaction mixture was heated to reflux
  2. customwas removed
  3. additionThen, water (200.0 ml) was added
  4. filtrationa dark-brown solid was collected by filtration
  5. customThe product was purified by silica gel column chromatography
  6. customThe final pure white product was obtained in the amount of 4.2 g (59.2%) by recrystallization from methanol/water

Sources & evidence

ORD record
ord-245d7fb2084446e6b09b0ba78263eebc
Source dataset
uspto-grants-2013_10
Patent number
US08546505B2

Reaction notes

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