Potassium Iodide → Methyl 5-cyano-2-iodobenzoate

HRID 321997Notes

Reaction equation

HRID 321997 reaction equation
N([O-])=O.[Na+].[CH3:5][O:6][C:7](=[O:17])[C:8]1[CH:13]=[C:12]([C:14]#[N:15])[CH:11]=[CH:10][C:9]=1N.[I-:18].[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>O.S(=O)(=O)(O)O>[CH3:5][O:6][C:7](=[O:17])[C:8]1[CH:13]=[C:12]([C:14]#[N:15])[CH:11]=[CH:10][C:9]=1[I:18]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 24477Sodium ThiosulfateHCID 10058039Methyl 2-amino-5-cyanobenzoateHCID 23668193Sodium Nitrite

Product 1

HCID 23076822Methyl 5-cyano-2-iodobenzoateYield 85.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 1118Sulfuric AcidSolvent

Procedure

Sodium nitrite (0.8 g, 11.4 mmol) in water (10 ml) was added dropwise over 10 minutes to a stirred solution of 2-amino-5-cyanobenzoic acid methyl ester (2.0 g, 11.4 mmol) in water (30 ml) and conc. sulphuric acid (15 ml) at 0° C. After a fiber 15 minutes at 5° C., a solution of potassium iodide (3.5 g, 21 mmol) in water (30 ml) was quickly added and the mixture allowed to warm to room temperature. 10% Aqueous sodium thiosulphate was added, the mixture extracted with ethyl acetate, the extract dried over magnesium sulphate and evaporated. The residue was purified by flash column chromatography on silica eluting with 20% ethyl acetate in hexane to yield the title compound as a colourless oil (2.8 g). MS (+EI) m/z 287 [M+].

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. dry with materialthe extract dried over magnesium sulphate
  3. customevaporated
  4. customThe residue was purified by flash column chromatography on silica eluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-23fb521a902b4ca39e84a61a9a257d11
Source dataset
uspto-grants-2001_04
Patent number
US06211189B1

Reaction notes

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