2-Fluorothiophenol → Ethyl 4-fluoro-alpha-[[(2-fluorophenyl)thio]methyl]benzeneacetate

HRID 22192

반응식

HRID 22192 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[CH2:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[SH:22].[O-]CC.[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:14][S:22][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[F:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 5202162-FluorothiophenolHCID 2723922Sodium ethoxideHCID 19736751Ethyl 2-(4-fluorophenyl)acrylate

생성물 1

HCID 19927552Ethyl 4-fluoro-alpha-[[(2-fluorophenyl)thio]methyl]benzeneacetate수율 82.2%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

The crude product from Step A (3.9 g, 20 mole) was taken up in 20 ml of ethanol. To this solution, being stirred at room temperature, was added 2-fluorothiophenol (2.5 g, 20 mmole) and 50 mg of solid sodium ethoxide. After stirring for eight hours the ethanol was concentrated and the residue taken up in ether. The ether mixture was washed twice with 15% NaOH solution, dried (MgSO4) and concentrated to a colorless oil (5.3 g, 82% yield). 1H NMR (CDCl3) δ: 7.28 (4H, m), 7.06 (4H, m), 4.13 (2H, m), 3.72 (1H, m), 3.55 (1H, m), 3.20 (1H, dd, J=6, 12 Hz), 1.21 (3H, t, J=6 Hz).

후처리

  1. concentrationwas concentrated
  2. washThe ether mixture was washed twice with 15% NaOH solution
  3. dry with materialdried (MgSO4)

출처 및 근거

ORD 기록
ord-c5b877e7aced48708173e5628ebd3f82
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428027

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