Toluene → HCID 12220705, compound

HRID 1365586Notes

Reaction equation

HRID 1365586 reaction equation
Br[C:2]1[C:19]2[C:10](=[CH:11][C:12]3[C:17](C=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.[C:20]1([CH3:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)(O)[O-].[Na+].C1(B(O)O)C=CC=CC=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.C(O)C>[C:20]1([C:26]2[C:19]3[C:10](=[CH:9][C:8]4[C:3]([CH:2]=3)=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH:11]=[C:12]3[C:17]=2[CH:16]=[CH:15][CH:14]=[CH:13]3)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 1140Toluene2×HCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 713579985-Bromotetracene

Product 1

HCID 12220705HCID 12220705, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
75 °C

Procedure

In a 100-ml round-bottomed flask equipped with a magnetic stirrer, were added 1.0 g (3.26 mmol) of 5-bromonaphthacene, 23 mg (0.0326 mmol) of dichlorobis(triphenylphosphine)palladium(II) catalyst and 12 ml of toluene. A solution containing 0.69 g (6.51 mmol) of sodium bicarbonate in 4 ml of water was added to the flask. The mixture was degassed via nitrogen purge for 10 minutes. A solution of 0.417 g (3.42 mmol) of phenylboronic acid in 12 ml of ethanol was then added to the flask, and the reaction mixture was heated to 75° C. and stirred overnight for 15 hours. The resulting reaction mixture contained yellow and white solids that were dissolved by the addition of toluene and water. The mixture was transferred to a 100-ml separatory funnel and the aqueous layer was extracted three times with 15 ml of toluene. After the toluene layer was back-extracted once with distilled water, it was stirred over sodium sulfate for one hour and filtered. Charcoal (2 g) was added to the toluene layer and stirred for a minimum of 2 hours. The charcoal was filtered off and the solvent was removed by rotary evaporation. The product was dried at room temperature under vacuum (product sublimed at higher temperatures). 5-Phenylnaphthacene was obtained in 93% yield (0.92 g) and used without further purification.

Workup

  1. customIn a 100-ml round-bottomed flask equipped with a magnetic stirrer
  2. additionwas added to the flask
  3. customThe mixture was degassed via nitrogen
  4. custompurge for 10 minutes
  5. customThe resulting reaction mixture
  6. customThe mixture was transferred to a 100-ml separatory funnel
  7. extractionthe aqueous layer was extracted three times with 15 ml of toluene
  8. extractionAfter the toluene layer was back-extracted once with distilled water, it
  9. stirringwas stirred over sodium sulfate for one hour
  10. filtrationfiltered
  11. additionCharcoal (2 g) was added to the toluene layer
  12. stirringstirred for a minimum of 2 hours
  13. filtrationThe charcoal was filtered off
  14. customthe solvent was removed by rotary evaporation
  15. customThe product was dried at room temperature under vacuum (product sublimed at higher temperatures)

Sources & evidence

ORD record
ord-7e8f6e179c204aa1a599005cb108ceb5
Source dataset
uspto-grants-2011_02
Patent number
US07892702B2

Reaction notes

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