Potassium Carbonate → 2-tert-Butyl-9,10-di(naphthalen-2-yl)anthracene

HRID 1438093Notes

Reaction equation

HRID 1438093 reaction equation
[C:1]([C:5]1[CH:18]=[CH:17][C:16]2[C:7](=[CH:8][C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].BrNC(=O)CCC(N)=O.C(C1C=C[C:43]2[C:34](=[C:35](Br)[C:36]3[C:41]([C:42]=2Br)=[CH:40][CH:39]=[CH:38][CH:37]=3)C=1)(C)(C)C.[CH:48]1[C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH:51]=[CH:50][C:49]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(O)C.C1(C)C=CC=CC=1.O>[CH3:3][C:1]([C:5]1[CH:18]=[CH:17][C:16]2[C:7](=[C:8]([C:43]3[CH:34]=[CH:35][C:36]4[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=4)[CH:42]=3)[C:9]3[C:14]([C:15]=2[C:50]2[CH:49]=[CH:48][C:57]4[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=4)[CH:51]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=1)([CH3:4])[CH3:2]

Participants

10

Reactant 5

HCID 11430Potassium CarbonateHCID 878002-tert-ButylanthraceneHCID 2734375(Naphthalen-2-yl)boronic acidHCID 41266109,10-dibromo-2-tert-butylanthraceneHCID 9834204N-Bromosuccinamide

Product 1

HCID 218960962-tert-Butyl-9,10-di(naphthalen-2-yl)anthracene

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent2×

Procedure

The 2-(t-butyl)anthracene (6.11g, 26.07 mmol) was placed into a 250 mL round bottom flask and was dissolved in dimethylformamide (80 mL) and was cooled on an ice bath. The N-bromosuccinamide (9.28g, 52.15 mmol) was dissolved in dimethylformamide (20 mL) and was added slowly to the reaction. After addition, the reaction was allowed to come to room temperature and was stirred for 3 hours. The mixture was poured into water (500 mL) and the solid collected, washed with water and then methanol. The product was collected, dried and then used directly in the next step. The 2-(t-butyl)-9,10-dibromoanthracene (9.8g, 24.99 mmol) was placed into a 250 mL round bottom flask along with 2-naphthylboronic acid (9.46g, 54.98 mmol), toluene (100 mL), ethanol (10 mL) and 2.0 aqueous potassium carbonate (75 mL). The reaction was purged with argon for 15 minutes and then Pd(PPh3)4 (0.29g) was added. The reaction was heated at reflux for 16 hours. The reaction was cooled and the organic layer was collected and washed with aqueous 5% HCI and then saturated aqueous brine solution. The organic layer was collected, dried and concentrated under reduced pressure. The compound was purified by flash chromatography with hexane and then dichloromethane which eluted the compound. Further purification was achieved by sublimation at 320° C. to give >99% purity of TBADN. This compound and its structure were confirmed by proton NMR analysis.

Workup

  1. temperaturewas cooled on an ice bath
  2. additionwas added slowly to the reaction
  3. additionAfter addition
  4. customto come to room temperature
  5. customthe solid collected
  6. washwashed with water
  7. customThe product was collected
  8. customdried
  9. customThe reaction was purged with argon for 15 minutes
  10. additionPd(PPh3)4 (0.29g) was added
  11. temperatureThe reaction was heated
  12. temperatureat reflux for 16 hours
  13. temperatureThe reaction was cooled
  14. customthe organic layer was collected
  15. washwashed with aqueous 5% HCI
  16. customThe organic layer was collected
  17. customdried
  18. concentrationconcentrated under reduced pressure
  19. customThe compound was purified by flash chromatography with hexane
  20. washdichloromethane which eluted the compound
  21. customFurther purification
  22. customwas achieved by sublimation at 320° C.

Sources & evidence

ORD record
ord-5166093cebc94fc6848ebe07577ed398
Source dataset
uspto-grants-2009_11
Patent number
US07622619B2

Reaction notes

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