Hydrochloric Acid → HCID 86081162, compound

HRID 2369757Notes

Reaction equation

HRID 2369757 reaction equation
Br[C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][C:9](Br)=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[CH:19]1([Mg]Br)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.Cl>C1COCC1.O1CCOCC1>[CH:19]1([C:2]2[C:15]3[C:16]4=[C:17]5[C:12](=[CH:13][CH:14]=3)[CH:11]=[CH:10][C:9]([CH:2]3[CH2:15][CH2:16][CH2:5][CH2:4][CH2:3]3)=[C:8]5[CH:7]=[CH:6][C:5]4=[CH:4][CH:3]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 176470Pyrene, 1,6-Dibromo-HCID 178419651HCID 178419651, compound

Product 1

HCID 86081162HCID 86081162, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

Under an atmospheric argon gas flow, 1,6-dibromopyrene in an amount of 20 g (55.6 millimole), cyclohexylmagnesiumbromide in an amount of 117 milliliter [117 millimole, 1 mole/liter (THF: tetrahydrofuran)], (diphenylphosphinoferrocene)palladium(II)dichloride in an amount of 2.27 g (5% by mole), dried dioxane in an amount of 80 milliliter and THF in an amount of 70 milliliter were placed into a three-neck flask equipped with a cooling pipe and having a capacity of 500 milliliter, and the resultant solution was stirred with heating at a temperature of 90° C. for 8 hours. After the completion of the reaction, adding 100 milliliter of dilute hydrochloric acid, an organic layer was separated and concentrated under a reduced pressure. Then, the organic layer was passed through a silicagel short column, and after concentrating under the reduced pressure again, a precipitated crystal was separated by filtration and as a result, 7.0 g of 1,6-dicyclohexylpyrene (pale yellow powder) was obtained (the yield: 71%).

Workup

  1. customequipped with a cooling pipe
  2. customAfter the completion of the reaction
  3. customan organic layer was separated
  4. concentrationconcentrated under a reduced pressure
  5. concentrationafter concentrating under the reduced pressure again
  6. customa precipitated crystal was separated by filtration and as a result

Sources & evidence

ORD record
ord-6c7a04299b5f47abb7687a2360440731
Source dataset
uspto-grants-2014_04
Patent number
US08709613B2

Reaction notes

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