Iodine → Methyl 2-amino-4-ethyl-5-iodobenzoate

HRID 906601Notes

Reaction equation

HRID 906601 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH3:11])=[CH:6][C:5]=1[NH2:12].[I:14]I>CCO.[O-]S([O-])(=O)=O.[Ag+].[Ag+]>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([I:14])[C:7]([CH2:10][CH3:11])=[CH:6][C:5]=1[NH2:12]

Participants

5

Reactant 2

HCID 807IodineHCID 59164409Methyl 2-amino-4-ethylbenzoate

Product 1

HCID 53424411Methyl 2-amino-4-ethyl-5-iodobenzoateYield 73%

Reagents, catalysts & solvents 2

HCID 159865Silver sulfateCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-amino-4-ethyl-benzoic acid methyl ester (500 mg, 2.79 mmol) in EtOH (2 mL) were added Ag2SO4 (868.15 mg, 2.79 mmol) and I2 (708.1 mg, 2.79 mmol) and the resultant mixture was stirred at r.t. for 3 h. The reaction mixture was filtered and the solvent was removed in vacuo. The residue was dissolved in EtOAc and the organic phase was washed with 1M Na2S2O3 and sat. aq NaHCO3. The solvent was removed in vacuo and the orange oil was purified by flash chromatography (silica gel, hexanes→4:1 hexanes:EtOAc) to provide the title compound (620 mg, 73%) as an orange solid. ESI-MS: m/z 306.2 [M+H]+, rt 6.03 min

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in EtOAc
  4. washthe organic phase was washed with 1M Na2S2O3 and sat. aq NaHCO3
  5. customThe solvent was removed in vacuo
  6. customthe orange oil was purified by flash chromatography (silica gel, hexanes→4:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-313fc481338a4cf48f81918726e9970b
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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