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

HRID 132639노트

반응식

HRID 132639 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-64fc2cfd7d9f4f349cc654d2b57705e2
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07388023B2

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