Cesium carbonate → 1-Cyclopropyl-3,5-dimethoxybenzene

HRID 41251노트

반응식

HRID 41251 반응식
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[CH:3]=1.C1(P(C2CCCCC2)[C:19]2C=CC=C[C:20]=2[C:25]2C(OC)=CC=CC=2OC)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:25]1([C:2]2[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[CH:3]=2)[CH2:20][CH2:19]1

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 6391871-Bromo-3,5-dimethoxybenzeneHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

생성물 1

HCID 582233921-Cyclopropyl-3,5-dimethoxybenzene수율 490.8%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매2회HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

To a solution of 1-bromo-3,5-dimethoxybenzene (2.00 g, 9.21 mmol) in dioxane (30 mL) and water (10 mL) were added potassium cyclopropyl trifluoroborate (2.73 g, 18.4 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (756 mg, 1.84 mmol), palladium(II) acetate (207 mg, 0.92 mmol) and cesium carbonate (18.0 g, 55.3 mmol), and the mixture was heated at 100° C. for 16 hours. After the reaction was completed, water was added to the reaction mixture, which was extracted with ethyl acetate and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-heptane/ethyl acetate: 3/1) to obtain the title compound (1.61 g, 9.03 mmol).

후처리

  1. extractionwas extracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (n-heptane/ethyl acetate: 3/1)

출처 및 근거

ORD 기록
ord-1febc6efb69144cd885e0f3d583c497d
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530504B2

반응 노트

불러오는 중…