四氧化硫 → 5-Chloro-4-fluoro-2-iodophenol

HRID 46366笔记

反应方程式

HRID 46366 反应方程式
[I:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:11]=[C:12]([OH:17])[CH:13]=[CH:14][C:15]=1[F:16].S(=O)(=O)(O)O.CCCCCCC>C(O)(=O)C>[Cl:9][C:10]1[C:15]([F:16])=[CH:14][C:13]([I:1])=[C:12]([OH:17])[CH:11]=1

参与物

6

反应物 4

HCID 1118四氧化硫HCID 8900正庚烷HCID 757903-氯-4-氟苯酚HCID 120273N-碘代丁二酰亚胺

产物 1

HCID 594364895-Chloro-4-fluoro-2-iodophenol收率 64.2%

试剂、催化剂与溶剂 1

HCID 176醋酸溶剂

实验过程

N-iodosuccinimide (4.61 g, 20.5 mmol), was suspended in glacial acetic acid (20 ml). To this suspension was added 3-chloro-4-fluorophenol (3.0 g, 20.0 mmol) and then concentrated sulphuric acid (0.36 ml, 6.14 mmol) was added dropwise over 5 minutes. The resulting brown/orange suspension was stirred at room temperature for 18 hours. The mixture was concentrated in vacuo and the residue was partitioned between water and dichloromethane, the dichloromethane was dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo to give an orange/red oil. The crude product was purified by column chromatography on silica gel using 1:1 ethyl acetate:heptane to give the title compound as a pale orange/brown solid (3.50 g, 60% yield)

后处理

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was partitioned between water and dichloromethane
  3. dry with materialthe dichloromethane was dried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give an orange/red oil
  7. customThe crude product was purified by column chromatography on silica gel using 1:1 ethyl acetate

来源与证据

ORD记录
ord-47aa5001d19741338414b8a49739c320
来源数据集
uspto-grants-2013_09
专利号
US08541588B2

反应笔记

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