2-Hydroxy-4-iodobenzoic acid → Methyl 4-iodosalicylate

HRID 1160790Notes

Reaction equation

HRID 1160790 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:12][Si](C=[N+]=[N-])(C)C>C1COCC1.CO>[CH3:12][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([I:11])=[CH:10][C:2]=1[OH:1]

Participants

5

Reactant 2

HCID 728742-Hydroxy-4-iodobenzoic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 11380407Methyl 4-iodosalicylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-hydroxy-4-iodo-benzoic acid (4.0 g, 0.015 mol) in THF (25 ml) and MeOH (25 ml) is treated by the dropwise addition of (trimethylsilyl)-diazomethane (2.0M in Et2O, 15 ml) and stirred at room temperature for 2.5 hours. Volatiles are removed in vacuo and the crude residue diluted into EtOAc. The organic phase is sequentially washed with saturated aqueous NaHCO3 (3×), saturated aqueous NaCl (1×), and H2O (1×). The organic phase is dried over MgSO4, filtered, and concentrated. The crude product is purified with silica gel column chromatography (0-80% ethyl acetate in hexanes gradient) to afford 2-hydroxy-4-iodo-benzoic acid methyl ester: ESMS m/z 279.0 (M+H+).

Workup

  1. customVolatiles are removed in vacuo
  2. additionthe crude residue diluted into EtOAc
  3. washThe organic phase is sequentially washed with saturated aqueous NaHCO3 (3×), saturated aqueous NaCl (1×), and H2O (1×)
  4. dry with materialThe organic phase is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified with silica gel column chromatography (0-80% ethyl acetate in hexanes gradient)

Sources & evidence

ORD record
ord-13bdf411e15d4ae4aae785599ab3c1a4
Source dataset
uspto-grants-2010_10
Patent number
US07816542B2

Reaction notes

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