Acetic Acid → 4-Fluoro-2-iodophenol

HRID 46302ノート

反応式

HRID 46302 の反応式
[I:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.C(O)(=O)C.S(=O)(=O)(O)O>O>[F:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([I:1])[CH:11]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 97324-FluorophenolHCID 120273N-Iodosuccinimide

生成物 1

HCID 101714174-Fluoro-2-iodophenol収率 40%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

N-Iodosuccinimide (10 g, 45.0 mmol) and 4-fluoro-phenol (5.00 g, 40.0 mmol) were suspended in acetic acid (39 ml, 649.0 mmol) and stirred for 5 minutes before addition of concentrated sulphuric acid (0.79 ml, 13.4 mmol). The reaction mixture was stirred for 18 hours at room temperature before diluting with water (100 ml). The aqueous layer was extracted with dichloromethane (2×30 ml). The combined organic extracts were washed with sodium thiosulphate solution (20% aqueous, wt:v), water, dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by column chromatography (silica gel) eluting with toluene to afford the title compound as an off white solid, 4.5 g, 40% yield.

後処理

  1. extractionThe aqueous layer was extracted with dichloromethane (2×30 ml)
  2. washThe combined organic extracts were washed with sodium thiosulphate solution (20% aqueous, wt:v), water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by column chromatography (silica gel)
  7. washeluting with toluene

出典と根拠

ORDレコード
ord-a229e06029324e1fb38eae258f9d1935
出典データセット
uspto-grants-2013_09
特許番号
US08541588B2

反応ノート

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