Iodine → 2-Chloro-5-iodo-1,3-dimethoxybenzene

HRID 62760ノート

反応式

HRID 62760 の反応式
[Cl:1][C:2]1[C:8]([O:9][CH3:10])=[CH:7][C:5](N)=[CH:4][C:3]=1[O:11][CH3:12].S(=O)(=O)(O)O.N([O-])=O.[Na+].[I-:22].[Na+].II.S([O-])([O-])(=O)=S.[Na+].[Na+]>O>[Cl:1][C:2]1[C:8]([O:9][CH3:10])=[CH:7][C:5]([I:22])=[CH:4][C:3]=1[O:11][CH3:12]

参加物

8

反応物 6

HCID 807IodineHCID 1118Sulfuric Acid2 回HCID 5238Sodium IodideHCID 24477Sodium ThiosulfateHCID 23668193Sodium NitriteHCID 670418354-Chloro-3,5-dimethoxybenzenamine

生成物 1

HCID 670417372-Chloro-5-iodo-1,3-dimethoxybenzene収率 68.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
0 °C

実験手順

4-Chloro-3,5-dimethoxyaniline (2) (6.61 g, 35.2 mmol) was added to a mixture of sulfuric acid (9.39 mL, 176 mmol) and H2O (100 mL) at 00° C. Sodium nitrite (3.16 g, 45.8 mmol) was added and the reaction mixture was stirred at 0° C. for 30 min. The mixture was added to a pre-warmed mixture of sodium iodide (21.1 g, 141 mmol), iodine (4.47 g, 17.6 mmol), sulphuric acid (8 mL) and H2O (100 mL) at 80° C. and the resulting mixture was heated at reflux for 30 min. The mixture was allowed to cool to RT and then 40% sodium thiosulfate solution (200 mL) was added. The product was extracted with EtOAc (300 mL), the solvent was removed in vacuo and the residue was purified by silica gel chromatography (120 g, 0-50% EtOAc in isohexanes) to afford 2-chloro-5-iodo-1,3-dimethoxybenzene (3) (7.16 g, 67% yield).

後処理

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 30 min
  3. temperatureto cool to RT
  4. extractionThe product was extracted with EtOAc (300 mL)
  5. customthe solvent was removed in vacuo
  6. customthe residue was purified by silica gel chromatography (120 g, 0-50% EtOAc in isohexanes)

出典と根拠

ORDレコード
ord-a7e27046576a44458eb50d74d470fc8c
出典データセット
uspto-grants-2016_09
特許番号
US09447028B2

反応ノート

読み込み中…