Sodium Carbonate → HCID 23160223, compound

HRID 1172777Notes

Reaction equation

HRID 1172777 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:6]3[C:11]([C:12]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1.[Cl:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=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.COCCOC>[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([C:2]2[CH:15]=[CH:14][C:13]3[C:4](=[C:5]([C:22]4[CH:23]=[CH:24][C:25]5[C:26](=[CH:22][CH:5]=[CH:6][CH:7]=5)[CH:27]=4)[C:6]4[C:11]([C:12]=3[C:16]3[CH:17]=[CH:18][C:19]5[C:20](=[CH:15][CH:2]=[CH:3][CH:4]=5)[CH:21]=3)=[CH:10][C:9]([C:32]3[CH:33]=[CH:34][C:29]([Cl:28])=[CH:30][CH:31]=3)=[CH:8][CH:7]=4)[CH:3]=2)=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 222471632-Bromo-9,10-diphenylanthracene

Product 1

HCID 23160223HCID 23160223, compoundYield 173.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

5.0 g (8.5 mmol) of 2-bromo-9,10-diphenylanthracene, 2.9 g (18.7 mmol) of 4-chlorophenylboronic acid, and 0.20 g (0.17 mmol) of tetrakis(triphenylphosphine)palladium were dissolved into 50 mL of 1,2-dimethoxyethane. Then, 25 mL of a 2 M aqueous solution of sodium carbonate were added, and the whole was refluxed under heating for 8 hours in an argon atmosphere. The resultant was stood to cool. After the completion of the reaction, the resultant was filtered, and the resultant solid was washed with water, methanol, and toluene to obtain 4.8 g of 2,6-bis(4-chlorophenyl)-9,10-di(2-naphthyl)anthracene (86% yield).

Workup

  1. temperaturethe whole was refluxed
  2. temperatureunder heating for 8 hours in an argon atmosphere
  3. temperatureto cool
  4. customAfter the completion of the reaction
  5. filtrationthe resultant was filtered
  6. washthe resultant solid was washed with water, methanol, and toluene

Sources & evidence

ORD record
ord-88d69832a3384abdaa9a7adb67f4166b
Source dataset
uspto-grants-2010_11
Patent number
US07833632B2

Reaction notes

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