Sodium Carbonate → 3-(Pyridin-3-yl)phenol

HRID 63384노트

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HRID 63384 반응식
Br[C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[N:9]1[CH:14]=[CH:13][CH:12]=[C:11](B(O)O)[CH:10]=1.C(=O)([O-])[O-].[Na+].[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]>[N:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:2]2[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=2)[CH:10]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 115633-BromophenolHCID 27343783-Pyridinylboronic acid

생성물 1

HCID 129379483-(Pyridin-3-yl)phenol수율 78.8%

시약·촉매·용매 2

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

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온도
120 °C

실험 절차

3-Bromophenol (500 mg, 2.86 mmol) and pyridin-3-ylboronic acid (422 mg, 3.76 mmol) were dissolved in dimethoxyethane/water=5 mL/2.5 mL. Pd(dppf)Cl2 (118 mg, 0.14 mmol) and sodium carbonate (919 mg, 8.67 mmol) were added thereto, 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 filtrate was added with water, and extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, and purified by column chromatography (hexane:ethyl acetate=9:1) to obtain 3-(pyridin-3-yl)phenol (386 mg, 78%).

후처리

  1. customAfter the completion of the reaction
  2. filtrationthe reaction mixture was filtered
  3. additionThe filtrate was added with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe obtained organic layer was dried over magnesium sulfate
  6. custompurified by column chromatography (hexane:ethyl acetate=9:1)

출처 및 근거

ORD 기록
ord-dfcc3666a7d64d84adcb20b07e17bb0f
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447083B2

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