Toluene → 2-(5-Trifluoromethylpyridine-2-yl)benzofuran

HRID 984754ノート

反応式

HRID 984754 の反応式
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.[O:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH:14]=[C:13]1B(O)O.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(OCC)(=O)C.C(O)C>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([C:13]2[O:12][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH:14]=2)=[N:3][CH:4]=1

参加物

9

反応物 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 2776266Benzo[b]furan-2-boronic acid

生成物 1

HCID 207673362-(5-Trifluoromethylpyridine-2-yl)benzofuran収率 17.7%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

In a 100 ml-three-necked flask, 2.80 g (15.4 mM) of 2-chloro-5-trifluoromethylpyridine, 2.50 g (15.4 mM) of 2-benzofuranylboronic acid, 14 ml of toluene, 7 ml of ethanol and 14 ml of 2M-sodium carbonate aqueous solution were placed and stirred at room temperature under nitrogen stream, and 0.55 g (0.48 mM) of tetrakis(triphenylphosphine)palladium (0) was added thereto. Thereafter, reflux under stirring for 4 hours was performed under nitrogen stream. After the reaction, the reaction mixture was cooled on an ice bath and stirred at room temperature after addition of ethyl acetate and saturated saline water. The organic layer was washed with water and dried with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain a residue. The residue was purified by alumina column chromatography (eluent: toluene) and recrystallized from methanol to obtain 0.72 g of 2-(5-trifluoromethylpyridine-2-yl)benzofuran (Yield: 17.7%).

後処理

  1. additionwas added
  2. temperatureThereafter, reflux
  3. customAfter the reaction
  4. temperaturethe reaction mixture was cooled on an ice bath
  5. stirringstirred at room temperature
  6. washThe organic layer was washed with water
  7. dry with materialdried with anhydrous magnesium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customto obtain a residue
  10. customThe residue was purified by alumina column chromatography (eluent: toluene)
  11. customrecrystallized from methanol

出典と根拠

ORDレコード
ord-b4e18f052c4a4a7d9bdc639c55b5c39d
出典データセット
uspto-grants-2005_03
特許番号
US06869694B2

反応ノート

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