Trimethylsilyl iodide → (Z)-2-bromo-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)benzoic acid

HRID 587675노트

반응식

HRID 587675 반응식
[Br:1][C:2]1[CH:12]=[C:11](/[CH:13]=[CH:14]\[CH:15]([C:20]2[CH:25]=[C:24]([Cl:26])[C:23]([Cl:27])=[C:22]([Cl:28])[CH:21]=2)[C:16]([F:19])([F:18])[F:17])[CH:10]=[CH:9][C:3]=1[C:4]([O:6]CC)=[O:5].I[Si](C)(C)C>CC#N>[Br:1][C:2]1[CH:12]=[C:11](/[CH:13]=[CH:14]\[CH:15]([C:20]2[CH:21]=[C:22]([Cl:28])[C:23]([Cl:27])=[C:24]([Cl:26])[CH:25]=2)[C:16]([F:19])([F:18])[F:17])[CH:10]=[CH:9][C:3]=1[C:4]([OH:6])=[O:5]

참가 물질

4

반응물 2

HCID 85247Trimethylsilyl iodideHCID 86675135(Z)-ethyl 2-bromo-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)benzoate

생성물 1

HCID 86675134(Z)-2-bromo-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)benzoic acid수율 42%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a stirred solution of (Z)-ethyl 2-bromo-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)benzoate (360 mg, 0.70 mmol) in CH3CN (1.0 mL) was added iodotrimethylsilane (0.28 mL, 2.8 mmol). The reaction mixture was heated to reflux for 20 h, allowed to cool to ambient temperature and partitioned between CH2Cl2 and aqueous 10% sodium thiosulfate (Na2S2O3). The organic phase was washed once with aqueous 10% Na2S2O3 and dried over magnesium sulfate (MgSO4) and concentrated in vacuo. Passing the material through a silica plug with 10% EtOAc in hexanes, followed by 20% MeOH in CH2Cl2) as the eluting solvents afforded the title compound as a yellow foam (143 mg, 42%): mp 54-64° C.; 1H NMR (400 MHz, CDCl3) δ 11.36 (s, 1H), 7.99 (d, J=8.0 Hz, 1H), 7.43 (s, 1H), 7.30 (s, 2H), 7.14 (d, J=7.9 Hz, 1H), 6.85 (d, J=11.4 Hz, 1H), 6.15 (t, J=10.9 Hz, 1H), 4.36-4.09 (m, 1H); 19F NMR (376 MHz, CDCl3) δ −69.30.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 20 h
  3. custompartitioned between CH2Cl2 and aqueous 10% sodium thiosulfate (Na2S2O3)
  4. washThe organic phase was washed once with aqueous 10% Na2S2O3
  5. dry with materialdried over magnesium sulfate (MgSO4)
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-2d19fbca522740ee8524632b43b8979b
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09226501B2

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