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

HRID 63384ノート

反応式

HRID 63384 の反応式
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

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 115633-BromophenolHCID 27343783-Pyridinylboronic acid

生成物 1

HCID 129379483-(Pyridin-3-yl)phenol収率 78.8%

試薬・触媒・溶媒 2

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

反応条件

温度
120 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-dfcc3666a7d64d84adcb20b07e17bb0f
出典データセット
uspto-grants-2016_09
特許番号
US09447083B2

反応ノート

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