Potassium Iodide → 1-Chloro-2-iodo-3-nitrobenzene

HRID 1521643

反応式

HRID 1521643 の反応式
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:3]=1N.N([O-])=O.[Na+].[I-:16].[K+]>Cl.O>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:3]=1[I:16]

参加物

6

反応物 3

HCID 4875Potassium IodideHCID 698552-Chloro-6-nitroanilineHCID 23668193Sodium Nitrite

生成物 1

HCID 227576901-Chloro-2-iodo-3-nitrobenzene

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒2 回

実験手順

2-chloro-6-nitroaniline (143-1; 1.0 g, 0.0058 mol) was dissolved in hydrochloric acid (10 mL) and cooled in an ice bath. Then a solution of sodium nitrite (0.68 g, 0.0098 mol) in water (10 mL) was added very slowly with stirring. After 15 min the reaction mixture was filtered through glass wool in to a solution of potassium iodide (4.1 g, 0.024 mol) in water (10 mL). The resulting orange mixture was stirred at room temperature overnight. Then it was extracted with ethyl acetate and washed with 10% aqueous sodium hydroxide solution (50 mL) solution. Organic layer was washed with saturated aqueous sodium chloride solution and concentrated under vacuum to obtain the title compound. 1H NMR (400 MHz, CDCl3) δ 7.854-7.835 (d, J=7.6 Hz, 1H), 7.788-7.768 (d, J=8 Hz, 1H), 7.624-7.584 (t, J=7.6 Hz, 1H).

後処理

  1. temperaturecooled in an ice bath
  2. stirringThe resulting orange mixture was stirred at room temperature overnight
  3. extractionThen it was extracted with ethyl acetate
  4. washwashed with 10% aqueous sodium hydroxide solution (50 mL) solution
  5. washOrganic layer was washed with saturated aqueous sodium chloride solution
  6. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-1317407172cc47b997de539cdb6dbe3f
出典データセット
uspto-grants-2015_07
特許番号
US09073929B2

関連ノート

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