Potassium Iodide → Methyl 5-cyano-2-iodobenzoate

HRID 2287345ノート

反応式

HRID 2287345 の反応式
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]

参加物

7

反応物 4

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

生成物 1

HCID 23076822Methyl 5-cyano-2-iodobenzoate収率 85.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒3 回HCID 1118Sulfuric Acid溶媒

実験手順

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 further 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+ ].

後処理

  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

出典と根拠

ORDレコード
ord-40d6ee9a766c434d825462ccc193124e
出典データセット
uspto-grants-2000_07
特許番号
US06083952

反応ノート

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