Potassium Phosphate, Tribasic → HCID 57702825, compound

HRID 221182Notes

Reaction equation

HRID 221182 reaction equation
C([C:7]1([CH2:26]CCCCC)[C:19]2[CH:18]=[C:17](B(O)O)[CH:16]=C[C:14]=2[C:13]2[C:8]1=[CH:9][C:10](B(O)O)=[CH:11][CH:12]=2)CCCCC.Br[C:33]1[CH:34]=[CH:35][C:36]([C:39]2[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=2)=[N:37][CH:38]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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>[N:37]1[CH:38]=[C:33]([C:11]2[CH:10]=[CH:9][C:8]3[C:7]4[C:19](=[CH:18][C:17]([C:33]5[CH:34]=[CH:35][C:36]([C:39]6[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=6)=[N:37][CH:38]=5)=[CH:16][CH:26]=4)[C:14]([CH2:26][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])([CH2:12][CH2:13][CH2:14][CH2:19][CH2:18][CH3:17])[C:13]=3[CH:12]=2)[CH:34]=[CH:35][C:36]=1[C:39]1[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 45242859,9-Dihexylfluorene-2,7-diboronic acidHCID 113906775-Bromo-2,3'-bipyridine

Product 1

HCID 57702825HCID 57702825, compoundYield 32.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Into a flask, 0.6 g of 9,9-dihexyl-fluorene-2,7-diboronic acid, 0.5 g of 5-bromo-2,3′-bipyridine, 115 mg of Pd(PPh3)4, 1.27 g of tripotassium phosphate, and 20 ml of toluene were put, and the solution was stirred at reflux temperature for 6.5 hours under argon atmosphere. After heating, the reaction liquid was cooled to room temperature, and washed by a saturated sodium chloride aqueous solution. The organic layer was concentrated in an evaporator, and the concentrates were purified by activated alumina column chromatography. The concentrates were recrystallized in a heptane/ethyl acetate mixed solvent, and thus 150 mg of 2,7-bis(2,3′-bipyridine-5-yl)-9,9-dihexylfluorene was obtained.

Workup

  1. temperatureat reflux temperature for 6.5 hours under argon atmosphere
  2. temperatureAfter heating
  3. customthe reaction liquid
  4. washwashed by a saturated sodium chloride aqueous solution
  5. concentrationThe organic layer was concentrated in an evaporator
  6. customthe concentrates were purified by activated alumina column chromatography
  7. customThe concentrates were recrystallized in a heptane/ethyl acetate mixed solvent

Sources & evidence

ORD record
ord-cca94b3ee1c74ea5a2ae2addabf41ab6
Source dataset
uspto-grants-2012_06
Patent number
US08202633B2

Reaction notes

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