Triisopropyl borate → 2-Dihydroxyboranyl-9,9-dioctylfluorene

HRID 1828616

反応式

HRID 1828616 の反応式
[Li]CCCC.Br[C:7]1[CH:19]=[CH:18][C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:9]=2[CH:8]=1.[B:36](OC(C)C)([O:41]C(C)C)[O:37]C(C)C>C1COCC1>[CH2:20]([C:10]1([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:9]2[CH:8]=[C:7]([B:36]([OH:41])[OH:37])[CH:19]=[CH:18][C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

参加物

5

反応物 3

HCID 21531Triisopropyl borateHCID 129646932-Bromo-9,9-di-n-octylfluoreneHCID 178418339Butyllithium

生成物 1

HCID 111338442-Dihydroxyboranyl-9,9-dioctylfluorene収率 89.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

n-BuLi (2.5 M in hexane, 12.0 mL, 30.0 mmol) is slowly added to a solution of 2-bromo-9,9-bis(n-octyl)fluorene (12.0 g, 25.6 mmol) in anhydrous THF (50 mL) at −78° C. At this temperature, the reaction mixture is stirred for 1 h before adding tri-iso-propyl borate (9.0 mL, 7.34 g, 39.0 mmol). The resulting mixture is then warmed to room temperature, stirred overnight followed by quenching with 100 mL HCl (2.0 M), and poured into a large amount of water. After extraction with ethyl ether three times, the organic portions are washed with brine before drying over anhydrous MgSO4. Solid residues collected by evaporating off the solvent are purified by column chromatography on silica gel with petroleum ether/ethyl acetate (2:1) to yield 9,9-bis(n-octyl)fluoren-2-yl-boronic acid (2a) as a white solid (10.0 g, 89%).

後処理

  1. stirringstirred overnight
  2. customby quenching with 100 mL HCl (2.0 M)
  3. additionpoured into a large amount of water
  4. extractionAfter extraction with ethyl ether three times
  5. washthe organic portions are washed with brine
  6. dry with materialbefore drying over anhydrous MgSO4
  7. customSolid residues collected
  8. customby evaporating off the solvent
  9. customare purified by column chromatography on silica gel with petroleum ether/ethyl acetate (2:1)

出典と根拠

ORDレコード
ord-68777ddcb6944665a0fb1e3ae2307484
出典データセット
uspto-grants-2006_06
特許番号
US07057009B2

関連ノート

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