Sodium Iodide → (S)-2,4-difluoro-1-(2-iodomethyl-butyl)-benzene

HRID 132646ノート

反応式

HRID 132646 の反応式
[F:1][C:2]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:3]=1[CH2:4][C@H:5]([CH2:12][CH3:13])[CH2:6]OS(C)(=O)=O.[I-:19].[Na+]>CC(C)=O>[F:1][C:2]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:3]=1[CH2:4][C@@H:5]([CH2:6][I:19])[CH2:12][CH3:13]

参加物

4

反応物 2

HCID 5238Sodium IodideHCID 87760874(2S)-methanesulfonic acid 2-(2,4-difluoro-benzyl)-butyl ester

生成物 1

HCID 69268259(S)-2,4-difluoro-1-(2-iodomethyl-butyl)-benzene収率 91.2%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A flask was charge with 9.54 g (34.3 mmol) of (2S)-methanesulfonic acid 2-(2,4-difluoro-benzyl)-butyl ester, 10.3 g (68.6 mmol) of sodium iodide, and 60 mL of acetone. The solution was heated at reflux for 30 hours. The acetone was removed under reduced pressure. The residue was partitioned between water and hexanes. The organic layer was collected and washed with sodium bisulfite solution and brine. The hexane was removed under reduced pressure, and the crude oil was purified by column chromatography (hexanes eluent). This procedure gave 9.7 g (91% yield) of the titled compound as a clear oil.

後処理

  1. temperatureThe solution was heated
  2. temperatureat reflux for 30 hours
  3. customThe acetone was removed under reduced pressure
  4. customThe residue was partitioned between water and hexanes
  5. customThe organic layer was collected
  6. washwashed with sodium bisulfite solution and brine
  7. customThe hexane was removed under reduced pressure
  8. customthe crude oil was purified by column chromatography (hexanes eluent)

出典と根拠

ORDレコード
ord-d421ab7bbf0a47adaa95bb9fca454bbf
出典データセット
uspto-grants-2008_06
特許番号
US07388023B2

反応ノート

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