Sodium Carbonate → 2-(3-Furanyl)-4,6-dimethylphenol

HRID 63370

반응식

HRID 63370 반응식
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[O:11]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12]1.C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])O.[Na+]>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]>[O:11]1[CH:15]=[CH:14][C:13]([C:2]2[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=2[OH:10])=[CH:12]1

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 2999762-Bromo-4,6-dimethylphenolHCID 516892Sodium BicarbonateHCID 2734358Furan-3-boronic acid

생성물 1

HCID 900027862-(3-Furanyl)-4,6-dimethylphenol수율 54%

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-Bromo-4,6-dimethylphenol (1.8 g, 8.9 mmol) was dissolved in dimethoxyethane/water (2:1). Furan-3-ylboronic acid (1 g, 8.9 mmol), Pd(dppf)Cl2 (0.36 g, 0.45 mmol) and sodium carbonate (3.7 g, 45 mmol) were added thereto, followed by stirring for 1 hour under reflux. After the completion of the reaction, the reaction mixture was added with a saturated sodium hydrogen carbonate aqueous solution, 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-(furan-3-yl)-4,6-dimethylphenol (0.9 g, 54%).

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-538299e6fa57496392fcca39dcb9cf07
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447083B2

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