Hydrochloric Acid → HCID 13694514, compound
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]=CC3=[CH:4][CH:3]=1.[CH:19]([Mg]Br)([CH3:21])[CH3:20].[CH2:24]1[CH2:28]O[CH2:26][CH2:25]1.Cl.O1CCOC[CH2:31]1>>[CH:25]([C:24]1[C:28]2[C:14]3=[C:13]4[C:2](=[CH:3][CH:4]=2)[CH:15]=[CH:16][C:17]([CH:8]([CH3:7])[CH3:9])=[C:12]4[CH:11]=[CH:10][C:21]3=[CH:19][CH:20]=1)([CH3:31])[CH3:26]Participants
Conditions
- Temperature
- 90 °C
Procedure
Under an atmospheric argon gas flow, 1,6-dibromopyrene in an amount of 20 g (55.6 millimole), isopropylmagnesiumbromide in an amount of 117 milliliter [117 millimole, 1 mole/liter (THF: tetrahydrofuran)], (diphenylphosphino ferrocene)palladium(II)dichloride in an amount of 2.27 g (5% by mole) and dried dioxane in an amount of 130 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, 7.4 g of 1,6-diisopropyl pyrene (pale yellow powder) was obtained (the yield: 31%).
Workup
- customequipped with a cooling pipe
- customAfter the completion of the reaction
- customan organic layer was separated
- concentrationconcentrated under a reduced pressure
- concentrationafter concentrating under the reduced pressure again
- customa precipitated crystal was separated by filtration and as a result
Sources & evidence
- ORD record
- ord-e7683c9eedb24eba9146772407e3a109
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08709613B2
Reaction notes
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