Dibenzofuran → HCID 21709773, compound

HRID 628243Notes

Reaction equation

HRID 628243 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[O:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.[CH2:19]([Li])[CH2:20][CH2:21][CH3:22].[O-][Si]([O-])=O.[Mg+2]>[Cu](Cl)Cl.O.CCCCCC>[C:1]1([C:19]2[C:16]3[C:17]4[CH:9]=[CH:1][CH:2]=[CH:3][C:18]=4[O:14][C:15]=3[CH:22]=[CH:21][CH:20]=2)[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 568DibenzofuranHCID 8028TetrahydrofuranHCID 61680MAGNESIUM SILICATE (synthetic)HCID 178418339Butyllithium

Product 1

HCID 21709773HCID 21709773, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 24014Cupric ChlorideCatalystHCID 962WaterSolventHCID 8058HexaneSolvent

Conditions

Temperature
-80 °C

Procedure

Into a 500-mL three-neck flask was put 6.0 g (35 mmol) of dibenzofuran, and the air in the flask was replaced with nitrogen. To this flask was added 100 mL of tetrahydrofuran (abbreviation: THF), and this solution was cooled down to −80° C. Then, 22 mL (35 mmol) of n-butyllithium (a 1.6 mol/L hexane solution) was dripped into this solution with a syringe. After that, this mixture solution was stirred for 2 hours while its temperature was increased to room temperature. After the stirring, the solution was cooled down to −80° C., 4.8 g (36 mmol) of copper(II) chloride was added thereto, and the mixture was stirred for 15 hours while its temperature was returned to room temperature. After the stirring, approximately 500 mL of water was added to this solution, followed by stirring for 1 hour to precipitate a solid. The precipitated solid was collected by suction filtration. The collected solid was dissolved in approximately 200 mL of hot toluene, this mixture was stirred and suction-filtered through Celite (Catalog No. 531-16855, produced by Wako Pure Chemical Industries, Ltd.), alumina, and Florisil (Catalog No. 540-00135, produced by Wako Pure Chemical Industries, Ltd.). The obtained filtrate was recrystallized from toluene/hexane to give 3.5 g of white powder, which was an objective substance, in 60% yield. Synthesis Scheme (c-1) of Step 1 is shown below.

Workup

  1. customInto a 500-mL three-neck flask was put
  2. temperaturewas increased to room temperature
  3. temperatureAfter the stirring, the solution was cooled down to −80° C.
  4. stirringthe mixture was stirred for 15 hours while its temperature
  5. customwas returned to room temperature
  6. stirringby stirring for 1 hour
  7. customto precipitate a solid
  8. filtrationThe precipitated solid was collected by suction filtration
  9. dissolutionThe collected solid was dissolved in approximately 200 mL of hot toluene
  10. stirringthis mixture was stirred
  11. filtrationsuction-filtered through Celite (Catalog No
  12. custom531-16855, produced by Wako Pure Chemical Industries, Ltd
  13. custom540-00135, produced by Wako Pure Chemical Industries, Ltd
  14. customThe obtained filtrate was recrystallized from toluene/hexane

Sources & evidence

ORD record
ord-11d5a0fc53814730b443daf4bb4cc867
Source dataset
uspto-grants-2016_04
Patent number
US09312498B2

Reaction notes

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