Sodium Carbonate → HCID 22065805, compound

HRID 1828617Notes

Reaction equation

HRID 1828617 reaction equation
[CH2:1]([C:9]1([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:21]2[CH:20]=[C:19](B(O)O)[CH:18]=[CH:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Br:33][C:34]1[CH:46]=[CH:45][C:44]2[C:43]3[C:38](=[CH:39][C:40](Br)=[CH:41][CH:42]=3)[C:37]([CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63])([CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[C:36]=2[CH:35]=1.C([O-])([O-])=O.[Na+].[Na+]>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>[Br:33][C:34]1[CH:35]=[C:36]2[C:44]([C:43]3[CH:42]=[CH:41][C:40]([C:19]4[CH:18]=[CH:17][C:16]5[C:15]6[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=6)[C:9]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[C:21]=5[CH:20]=4)=[CH:39][C:38]=3[C:37]2([CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63])[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])=[CH:45][CH:46]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 52153212,7-Dibromo-9,9-di-n-octylfluoreneHCID 111338442-Dihydroxyboranyl-9,9-dioctylfluorene

Product 1

HCID 22065805HCID 22065805, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 9,9-bis(n-octyl)fluoren-2-yl-boronic acid (2a) (2.0 g, 4.60 mmol), 2,7-dibromo-9,9-bis(n-octyl)fluorene (3a) (4.0 g, 7.32 mmol), Pd(PPh3)4 (50 mg, 0.043 mmol), Na2CO3 (2.0 M aqueous solution, 12.0 mL, 24.0 mmol), and toluene (20 mL) is stirred at 90° C. for 2 days. After the mixture is cooled to room temperature, 200 mL of petroleum ether is added to the reaction mixture. The organic portion is separated and washed with brine before drying over anhydrous MgSO4. The solvent is evaporated off, and the solid residues are purified by column chromatography on silica gel with petroleum ether to afford 7-bromo-9,9,9′,9′-tetra-n-octyl-2,2′-bifluorene (4a) as a white solid (2.52 g, 66%).

Workup

  1. temperatureAfter the mixture is cooled to room temperature
  2. customThe organic portion is separated
  3. washwashed with brine
  4. dry with materialbefore drying over anhydrous MgSO4
  5. customThe solvent is evaporated off
  6. customthe solid residues are purified by column chromatography on silica gel with petroleum ether

Sources & evidence

ORD record
ord-1a4941c5a3c14dc2a96fd95684f0cd25
Source dataset
uspto-grants-2006_06
Patent number
US07057009B2

Reaction notes

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