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2-Bromopyridine → 2-(4-Vinylphenyl)pyridine

HRID 431842
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HRID 431842 반응식
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)=O.Br[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.O1CCC[CH2:20]1.C(=O)([O-])[O-].[K+].[K+]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:5][CH:4]=1)=[CH2:20]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 79732-BromopyridineHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 5910734-Formylphenylboronic Acid

생성물 1

HCID 117152892-(4-Vinylphenyl)pyridine수율 80%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매
HCID 962
Water
용매

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온도
90 °C

실험 절차

4-Formylphenylboronic acid (10.14 g, 0.0676 mol), 2-bromopyridine (12.64 g, 0.08 mol), tetrahydrofuran (100 ml), 2M potassium carbonate aqueous solution (26 ml), and palladium acetate (Pd(OAc)2, 0.04 g, 1 mol %) were placed into 250 ml of 2-necked round-bottomed flask under N2. The reaction mixture was refluxed at 90° C. for 24 hr and then poured in 200 ml of water in beaker. The reaction mixture was extracted with ether (3×150 ml) and the ether layer was then dried over magnesium sulfate (10 g) by stirring for 30 min. The dried ether layer was evaporated in vacuo to dryness and purified further by column chromatography on silica gel with eluting hexane/ethylacetate (1/5) to yield 2-(4-vinyl-phenyl)pyridine (80%).

후처리

  1. extractionThe reaction mixture was extracted with ether (3×150 ml)
  2. dry with materialthe ether layer was then dried over magnesium sulfate (10 g)
  3. customThe dried ether layer was evaporated in vacuo to dryness
  4. custompurified further by column chromatography on silica gel with eluting hexane/ethylacetate (1/5)

출처 및 근거

ORD 기록
ord-c86faa2f25644721a3f27faa45d993a0
출처 데이터셋
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06660821B2

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