Water → 4-(3-Furanyl)-2,6-dimethylphenol

HRID 63373

반응식

HRID 63373 반응식
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=1.[O:11]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12]1.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.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])[C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=2)=[CH:12]1

참가 물질

7

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 169194-Bromo-2,6-dimethylphenolHCID 2734358Furan-3-boronic acid

생성물 1

HCID 900025234-(3-Furanyl)-2,6-dimethylphenol수율 68.7%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
120 °C

실험 절차

4-Bromo-2,6-dimethylphenol (350 mg, 1.74 mmol), 3-furanylboronic acid (269 mg, 2.26 mmol), Pd(dppf)Cl2 (71 mg, 0.087 mmol) and sodium carbonate (553 mg, 5.22 mmol) were dissolved in DME:water=4 mL:2 mL, followed by stirring in microwave at 120° C. for 20 minutes. After the completion of the reaction, the reaction mixture was filtered using Celite. The obtained filtrate was extracted with ethyl acetate, dried over magnesium sulfate, and purified by column chromatography (hexane:ethyl acetate=9:1) to obtain 4-(furan-3-yl)-2,6-dimethylphenol (225 mg, 50%).

후처리

  1. customAfter the completion of the reaction
  2. filtrationthe reaction mixture was filtered
  3. extractionThe obtained filtrate was extracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. custompurified by column chromatography (hexane:ethyl acetate=9:1)

출처 및 근거

ORD 기록
ord-2de7987e35f7458f8887fa5fbfa415af
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447083B2

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