Ethanol → 2,7-bis(5-methoxybiphenyl-2-yl)-9,9-dimethyl-9H-fluorene

HRID 1753701노트

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HRID 1753701 반응식
Br[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8](Br)=[CH:9][CH:10]=3)[C:5]([CH3:17])([CH3:16])[C:4]=2[CH:3]=1.[CH3:18][O:19][C:20]1[CH:21]=[CH:22][C:23](B(O)O)=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:25]=1.[C:35]([O-:38])([O-])=O.[Na+].[Na+].[CH3:41][CH2:42]O>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.C1(C)C=CC=CC=1>[CH3:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([C:2]2[CH:14]=[CH:13][C:12]3[C:11]4[C:6](=[CH:7][C:8]([C:2]5[CH:14]=[CH:13][C:12]([O:38][CH3:35])=[CH:4][C:3]=5[C:41]5[CH:42]=[CH:7][CH:6]=[CH:5][CH:16]=5)=[CH:9][CH:10]=4)[C:5]([CH3:17])([CH3:16])[C:4]=3[CH:3]=2)=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:25]=1

참가 물질

7

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 121238762,7-Dibromo-9,9-dimethylfluoreneHCID 85664000(4-Methoxy-2-phenylphenyl)boronic acid

생성물 1

HCID 867300012,7-bis(5-methoxybiphenyl-2-yl)-9,9-dimethyl-9H-fluorene수율 67%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

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온도
110 °C

실험 절차

A mixture of 3.52 g (10 mmol) of 2,7-dibromo-9,9-dimethyl-9H-fluorene, 5.5 g (24 mmol) of 5-methoxybiphenyl-2-ylboronic acid, 0.12 g (0.1 mmol) of tetrakis(triphenylphosphine)palladium, 15 ml of 2M Na2CO3, 20 ml of EtOH and 60 ml toluene was degassed and placed under nitrogen, and then heated at 110° C. for 8 h. After finishing the reaction, the mixture was allowed to cool to room temperature. The reaction mixture was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was evaporated in vacuum. The residue was purified by column chromatography on silica(hexane-dichloromethane) afforded a white solid (3.7 g, 6.7 mmol, 67%); 1H NMR (CDCl3, 400 MHz): chemical shift (ppm) 7.57 (d, J=8.00 Hz, 2H), 7.45 (d, J=9.20 Hz, 2H), 7.21˜7.14 (m, 12H), 7.00˜6.98 (m, 4H), 6.88 (s, 2H), 3.89 (s, 6H), 0.89 (s, 6H).

후처리

  1. customwas degassed
  2. customthe reaction
  3. temperatureto cool to room temperature
  4. extractionThe reaction mixture was extracted with ethyl acetate and water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customthe solvent was evaporated in vacuum
  7. customThe residue was purified by column chromatography on silica(hexane-dichloromethane)

출처 및 근거

ORD 기록
ord-a6fe55e51823493db529d86b94f5fb20
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09166177B2

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