Potassium Iodide → Methyl 5-cyano-2-iodobenzoate

HRID 321997노트

반응식

HRID 321997 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매3회HCID 1118Sulfuric Acid용매

실험 절차

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+].

후처리

  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

출처 및 근거

ORD 기록
ord-23fb521a902b4ca39e84a61a9a257d11
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211189B1

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