1,2-Dimethoxyethane → 9,9-Diethyl-2,7-bis(4-octyloxybiphenyl-4'-yl)fluorene

HRID 1269126

반응식

HRID 1269126 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]([CH2:18][CH3:19])([CH2:16][CH3:17])[C:4]=2[CH:3]=1.[CH2:20]([O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=2)=[CH:31][CH:30]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].C(=O)([O-])[O-].[Na+].[Na+].CO[CH2:52][CH2:53][O:54][CH3:55]>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.O>[CH2:16]([C:5]1([CH2:18][CH3:19])[C:4]2[CH:3]=[C:2]([C:38]3[CH:39]=[CH:40][C:35]([C:32]4[CH:33]=[CH:34][C:29]([O:28][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:30][CH:31]=4)=[CH:36][CH:37]=3)[CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][C:8]([C:29]1[CH:30]=[CH:31][C:32]([C:35]3[CH:36]=[CH:37][C:53]([O:54][CH2:55][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH3:20])=[CH:52][CH:40]=3)=[CH:33][CH:34]=1)=[CH:9][CH:10]=2)[CH3:17]

참가 물질

7

반응물 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 35310452,7-Dibromo-9,9-diethylfluoreneHCID 108535444-Octyloxybiphenyl-4'-yl boronic acid

생성물 1

HCID 219245109,9-Diethyl-2,7-bis(4-octyloxybiphenyl-4'-yl)fluorene수율 65%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매

실험 절차

Tetrakis(triphenylphosphine)palladium(0) (0.70 g, 0.0006 mol) was added to a stirred solution of 2,7-dibromo-9,9-diethylfluorene (4) (2.33 g, 0.0061 mol), 4-octyloxybiphenyl-4′-yl boronic acid (5.00 g, 0.0153 mol), 20% sodium carbonate solution (100 cm3) and 1,2-dimethoxyethane (150 cm3). The reaction mixture was heated under reflux overnight. Water (300 cm3) was added to the cooled reaction mixture and the product extracted into DCM (3×300 cm3). The combined organic extracts were washed with brine (2×150 cm3), dried (MgSO4)), filtered and the filtrate evaporated down under partially reduced pressure. The residue was purified by column chromatography on silica gel using DCM and hexane (30:70) as eluent and recrystallisation from ethanol and DCM to yield a white crystalline solid (3.10 g, 65%, m.pt. 146° C.).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux overnight
  3. extractionthe product extracted into DCM (3×300 cm3)
  4. washThe combined organic extracts were washed with brine (2×150 cm3)
  5. dry with materialdried (MgSO4)),
  6. filtrationfiltered
  7. customthe filtrate evaporated down under partially reduced pressure
  8. customThe residue was purified by column chromatography on silica gel
  9. customrecrystallisation from ethanol and DCM

출처 및 근거

ORD 기록
ord-fe377bf543b84fe482f727ff0328144d
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199167B2

연결된 노트

불러오는 중…