Sulfuric Acid → 6-Chloro-3'-fluoro-4-iodobiphenyl-3-ol

HRID 1619700ノート

反応式

HRID 1619700 の反応式
[I:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=[CH:14][C:13]([OH:23])=[CH:12][CH:11]=1.S(=O)(=O)(O)O>C(O)(=O)C.ClCCl>[Cl:9][C:10]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=[CH:14][C:13]([OH:23])=[C:12]([I:1])[CH:11]=1

参加物

6

反応物 3

HCID 1118Sulfuric AcidHCID 120273N-IodosuccinimideHCID 580422636-Chloro-3'-fluorobiphenyl-3-ol

生成物 1

HCID 580423086-Chloro-3'-fluoro-4-iodobiphenyl-3-ol収率 47.7%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

N-Iodosuccinimide (261 mg, 1.16 mmol) was added to a mixture of 6-chloro-3′-fluorobiphenyl-3-ol (Preparation 100, 270 mg, 1.21 mmol) and concentrated sulphuric acid (24 μL, 0.43 mmol) in acetic acid (3 mL) and dichloromethane (3 mL). The reaction mixture was stirred at room temperature for 1.5 hours. The reaction mixture was diluted with dichloromethane (10 mL) and washed with sodium metabisulfite (0.5M, 10 mL), dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography eluting with heptane:dichloromethane (70:30) to give the title compound (193 mg, 46%) as a pale yellow solid.

後処理

  1. washwashed with sodium metabisulfite (0.5M, 10 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography
  6. washeluting with heptane:dichloromethane (70:30)

出典と根拠

ORDレコード
ord-36f9ba5dc32a49219546082825a47ee2
出典データセット
uspto-grants-2014_07
特許番号
US08772293B2

反応ノート

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