Water → 3-(2-Hydroxyphenyl)pyridine

HRID 63374

반응식

HRID 63374 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[N:9]1[CH:14]=[CH:13][CH:12]=[C:11](B(O)O)[CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C(COC)OC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[N:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[OH:8])[CH:10]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 72442-BromophenolHCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acid

생성물 1

HCID 125036743-(2-Hydroxyphenyl)pyridine수율 50.4%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 18180031Water 1,2-dimethoxyethane용매

실험 절차

2-Bromophenol (0.5 g, 2.9 mmol) was dissolved in dimethoxyethane/water (2:1). Pyridin-3-ylboronic acid (0.71 g, 5.8 mmol) and Pd(dppf)Cl2 (0.12 g, 0.14 mmol), sodium carbonate (1.2 g, 14 mmol) were added thereto, followed by stirring for 1 hour under reflux. After the completion of the reaction, the reaction mixture was added with water, and extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, concentrated under reduced pressure, and purified by column chromatography to obtain 2-(pyridin-3-yl)phenol (0.25 g, 20%).

후처리

  1. temperatureunder reflux
  2. customAfter the completion of the reaction
  3. extractionextracted with ethyl acetate
  4. dry with materialThe obtained organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-95095235c5cc4695bc5b6653df5da0b5
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447083B2

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