1,4-Dioxane → Triphenylen-2-ylboronic acid

HRID 467419노트

반응식

HRID 467419 반응식
FC(F)(F)S(O[C:7]1[C:24]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]=2[CH:10]=[CH:9][CH:8]=1)(=O)=O.[B:27]1(B2OC(C)(C)C(C)(C)O2)[O:31]C(C)(C)C(C)(C)[O:28]1.C([O-])(=O)C.[K+].O1CCOCC1>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O>[CH:7]1[C:24]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]=2[CH:10]=[CH:9][C:8]=1[B:27]([OH:31])[OH:28]

참가 물질

7

반응물 4

HCID 312751,4-DioxaneHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 86647724Triphenylenyl trifluoromethanesulfonate

생성물 1

HCID 59805119Triphenylen-2-ylboronic acid수율 51.9%

시약·촉매·용매 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 962Water용매

실험 절차

Under an argon atmosphere, 37.6 g of triphenylenyl trifluoromethanesulfonate, 27.9 g of bis(pinacolato)diboron, 2.45 g of 1,1′-bis(diphenylphosphino)ferrocene palladium (II) dichloride dichloromethane complex, 1.66 g of 1,1′-bis(diphenylphosphino)ferrocene and 29.4 g of potassium acetate were placed in a flask. 600 mL of anhydrous dioxane was added thereto, and the resultant was refluxed with stirring while heating for 8 hours. After cooling to room temperature, 300 mL of water was added to the reaction solution, followed by extraction with toluene. An aqueous phase was removed, and an organic phase was washed with water and saturated brine, and then dried with magnesium sulfate. Magnesium sulfate was removed and the solvent was distilled under reduced pressure. The resulting residue was purified by means of silica gel column chromatography, whereby 14.1 g (yield: 40%) of triphenylene-2-boronic acid picohal ester was obtained.

후처리

  1. temperaturethe resultant was refluxed
  2. temperaturewhile heating for 8 hours
  3. extractionfollowed by extraction with toluene
  4. customAn aqueous phase was removed
  5. washan organic phase was washed with water and saturated brine
  6. dry with materialdried with magnesium sulfate
  7. customMagnesium sulfate was removed
  8. distillationthe solvent was distilled under reduced pressure
  9. customThe resulting residue was purified by means of silica gel column chromatography

출처 및 근거

ORD 기록
ord-f5ac206fbc5c480bab33cb7f2000af89
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623520B2

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