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

HRID 1828616

반응식

HRID 1828616 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 111338442-Dihydroxyboranyl-9,9-dioctylfluorene수율 89.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-68777ddcb6944665a0fb1e3ae2307484
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07057009B2

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