Methanol → Methyl 3-iodo-5-nitrobenzoate

HRID 2278715Notes

Reaction equation

HRID 2278715 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6].[CH3:14]O.S(Cl)(Cl)=O>>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([O:7][CH3:14])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 805803-Iodo-5-nitrobenzoic acid

Product 1

HCID 7020599Methyl 3-iodo-5-nitrobenzoate

Procedure

To a stirred solution of 3-iodo-5-nitrobenzoic acid (15.1 g, 0.049 mol) in methanol (151 mL, 3.73 mol) was added thionyl chloride (15.1 mL, 0.205 mol) dropwise at 0° C. The mixture was heated to reflux for 2 hours. The solvent was removed in vacuo. The residue was purified by flash chromatography (0-100% EtOAc/hexane) to afford an white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. customThe solvent was removed in vacuo
  4. customThe residue was purified by flash chromatography (0-100% EtOAc/hexane)
  5. customto afford an white solid

Sources & evidence

ORD record
ord-230ff938fff145e8adf65166834106d1
Source dataset
uspto-grants-2015_09
Patent number
US09133122B2

Reaction notes

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