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

HRID 467419ノート

反応式

HRID 467419 の反応式
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]

参加物

7

反応物 4

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

生成物 1

HCID 59805119Triphenylen-2-ylboronic acid収率 51.9%

試薬・触媒・溶媒 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f5ac206fbc5c480bab33cb7f2000af89
出典データセット
uspto-grants-2014_01
特許番号
US08623520B2

反応ノート

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