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

HRID 984140ノート

反応式

HRID 984140 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-902e7ca74f6a4554a658e82f8791c8cd
出典データセット
uspto-grants-2005_03
特許番号
US06867243B2

反応ノート

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