Potassium Carbonate → 9-(2-Naphthyl)-10-triphenysilyl anthracene

HRID 270736Notes

Reaction equation

HRID 270736 reaction equation
Br[C:2]1[C:3]2[C:8]([C:9]([Si:16]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[CH:35]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:38]=[CH:37][C:36]=1B(O)O.C([O-])([O-])=O.[K+].[K+]>COCCOC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:35]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:38]=[CH:37][C:36]=1[C:2]1[C:15]2[C:10]([C:9]([Si:16]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:8]3[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]3)=[CH:11][CH:12]=[CH:13][CH:14]=2

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2734375(Naphthalen-2-yl)boronic acidHCID 598339599-Bromo-l0-triphenysilyl anthracene

Product 1

HCID 598339589-(2-Naphthyl)-10-triphenysilyl anthracene

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

9-bromo-10-triphenysilyl anthracene (4 g, 7.8 mmol), 2-naphthylboronic acid (1.6 g, 9.4 mmol) and K2CO3 (1.5 g,15.6 mmol) were dissolved in the solvent mixture of 50 mL ethylene glycol dimethyl ether and 75 mL water. The stirred solution was added tetrakis (triphenylphosphine) palladium (0) and the mixture refluxed under N2 for 16 hours. The reaction mixture was cooled and the water extracted with acetyl acetate three times. The combined organic phase was washed with portions of brine. The organic layer was then dried with MgSO4, filtered, and evaporated of solvent. The crude material was purified by column chromatography (n-hexane/acetyl acetate=10/1) to give 9-(2-naphthyl)-10-triphenysilyl anthracene (Compound 2), the reaction was following:

Workup

  1. temperaturethe mixture refluxed under N2 for 16 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionthe water extracted with acetyl acetate three times
  4. washThe combined organic phase was washed with portions of brine
  5. dry with materialThe organic layer was then dried with MgSO4
  6. filtrationfiltered
  7. customevaporated of solvent
  8. customThe crude material was purified by column chromatography (n-hexane/acetyl acetate=10/1)

Sources & evidence

ORD record
ord-593ab732c5ec421ba75b5e0d6f386ad3
Source dataset
uspto-grants-2008_11
Patent number
US07449593B2

Reaction notes

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