Potassium Carbonate → 1,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene

HRID 242393

반응식

HRID 242393 반응식
[F:1][C:2]([F:6])([F:5])[CH:3]=[CH2:4].C(=O)([O-])[O-].[K+].[K+].[Cl:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[C:18]([Cl:20])[CH:19]=1>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:13][C:14]1[CH:15]=[C:16]([C:3]([C:2]([F:6])([F:5])[F:1])=[CH2:4])[CH:17]=[C:18]([Cl:20])[CH:19]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 126723,3,3-TrifluoropropeneHCID 27343313,5-Dichlorophenylboronic acid

생성물 1

HCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

3,3,3-Trifluoropropene (3.2 g), potassium carbonate (4.6 g) and bis-(triphenylphosphine)-palladium chloride (0.2 g) is added to a solution of 3,5-dichlorophenylboronic acid in THF (20 ml) under nitrogen. After 3 hours at reflux, the reaction is quenched with ethyl acetate (50 ml) and water (50 ml). The organic phase is then extracted with water and with a saturated aqueous solution of NaCl, dried over Na2SO4 and concentrated in vacuo. The crude product is purified on silica gel (35×45 mm) using heptane (150 ml) as eluant to yield 1,3-dichloro-5-(1-trifluoromethyl-vinyl)-benzene (2.7 g), as a colorless oil. MS (HPLC/MS): no ionisation. Retention time: 5.10 min.

후처리

  1. temperatureAfter 3 hours at reflux
  2. customthe reaction is quenched with ethyl acetate (50 ml) and water (50 ml)
  3. extractionThe organic phase is then extracted with water and with a saturated aqueous solution of NaCl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified on silica gel (35×45 mm)

출처 및 근거

ORD 기록
ord-0ce6ebe3c44b4fac9a3a3d6c739dec98
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653116B2

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