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

HRID 62760노트

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HRID 62760 반응식
[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]

참가 물질

8

반응물 6

HCID 807IodineHCID 1118Sulfuric Acid2회HCID 5238Sodium IodideHCID 24477Sodium ThiosulfateHCID 23668193Sodium NitriteHCID 670418354-Chloro-3,5-dimethoxybenzenamine

생성물 1

HCID 670417372-Chloro-5-iodo-1,3-dimethoxybenzene수율 68.1%

시약·촉매·용매 1

HCID 962Water용매2회

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온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-a7e27046576a44458eb50d74d470fc8c
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447028B2

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