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

HRID 1243252

Reaction equation

HRID 1243252 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-6a4fea84442e46e2a65c4e8f66d7073d
Source dataset
uspto-grants-2006_10
Patent number
US07118787B2

Linked notes

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