Cesium carbonate → HCID 21252717, 화합물

HRID 1676185노트

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HRID 1676185 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br/[CH:19]=[CH:20]/[C:21]([F:24])([F:23])[F:22].C(=O)([O-])[O-].[Cs+].[Cs+]>O.CN(C=O)C.CCOC(C)=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:19]=[CH:20]/[C:21]([F:24])([F:23])[F:22])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 27343144-Benzyloxy-phenylboronic acidHCID 57083831-Bromo-3,3,3-trifluoroprop-1-ene

생성물 1

HCID 21252717HCID 21252717, 화합물수율 74.3%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
90 °C

실험 절차

A mixture of 4-(benzyloxy)phenylboronic acid (1026 mg, 4.50 mmol, Alfa Aesar), (E)-1-bromo-3,3,3-trifluoroprop-1-ene (262 mg, 1.5 mmol, SynQuest), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (122 mg, 0.15, Combiphos Catalysts, Inc.) and cesium carbonate (2444 mg, 7.50 mmol, Aldrich) in Water (0.5 mL) and DMF (3.0 mL) was heated under microwave conditions (90° C., 20 min). The reaction mixture was diluted with EtOAc and filtered. The filtrate was washed with water and brine, dried (Na2SO4) and concentrated in vacuo. The residual was purified by flash chromatography on silica gel (0 to 100% EtOAc/hexanes) to yield the title compound (310 mg, 74%) as a pale yellow solid.

후처리

  1. filtrationfiltered
  2. washThe filtrate was washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residual was purified by flash chromatography on silica gel (0 to 100% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-c5404490f8a94fb68f5cbbc55ddc4323
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003796B2

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