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

HRID 984754노트

반응식

HRID 984754 반응식
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

참가 물질

9

반응물 4

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

생성물 1

HCID 207673362-(5-Trifluoromethylpyridine-2-yl)benzofuran수율 17.7%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-b4e18f052c4a4a7d9bdc639c55b5c39d
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06869694B2

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