4,4'-Dichlorobenzophenone → 6,6-Di(p-chlorophenyl)fulvene

HRID 423125Notes

Reaction equation

HRID 423125 reaction equation
[CH:1]1[CH2:5][CH:4]=[CH:3][CH:2]=1.CCCCCC.C([Li])CCC.[Cl:17][C:18]1[CH:32]=[CH:31][C:21]([C:22]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)=O)=[CH:20][CH:19]=1>O1CCCC1>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)=[C:2]2[CH:1]=[CH:5][CH:4]=[CH:3]2)=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 70344,4'-DichlorobenzophenoneHCID 7612CyclopentadieneHCID 8058HexaneHCID 178418339Butyllithium

Product 1

HCID 118334636,6-Di(p-chlorophenyl)fulveneYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A reaction vessel equipped with a dropping funnel was charged with 40 ml of dehydrated tetrahydrofuran and 2.15 ml (25.9 mmol) of cyclopentadiene under nitrogen atmosphere, and 18.0 ml (28.5 mmol) of a hexane solution of n-butyllithium of 1.58 mol/L was added dropwise and stirred while cooling the above solution at 0° C. Then, a solution prepared by dissolving 5.00 g (19.9 mmol) of 4,4′-dichlorobenzophenone in 30 ml of dehydrated tetrahydrofuran was placed in the dropping funnel and added dropwise while cooling at 0° C., and the solution was allowed to return to room temperature and stirred for one day. This reaction solution was extracted with diethyl ether, and the separated organic layer was washed with 1N hydrochloric acid, a saturated sodium hydrogen carbonate aqueous solution and a saturated salt solution and dried over anhydrous magnesium sulfate. Then, magnesium sulfate was removed by filtration, and the solvent contained in the filtrate was removed by distillation under reduced pressure by means of a rotary evaporator. The residue was purified through a silica gel column to obtain a targeted product (amount obtained: 3.37 g, yield: 57%). The targeted product was identified by means of 1H-NMR.

Workup

  1. customA reaction vessel equipped with a dropping funnel
  2. customThen, a solution prepared
  3. additionadded dropwise
  4. temperaturewhile cooling at 0° C.
  5. customto return to room temperature
  6. stirringstirred for one day
  7. extractionThis reaction solution was extracted with diethyl ether
  8. washthe separated organic layer was washed with 1N hydrochloric acid
  9. dry with materiala saturated sodium hydrogen carbonate aqueous solution and a saturated salt solution and dried over anhydrous magnesium sulfate
  10. customThen, magnesium sulfate was removed by filtration
  11. customwas removed by distillation under reduced pressure by means of a rotary evaporator
  12. customThe residue was purified through a silica gel column
  13. customto obtain
  14. customa targeted product (amount obtained: 3.37 g, yield: 57%)

Sources & evidence

ORD record
ord-25a52cdb25934737a05a53dce1f5dbf6
Source dataset
uspto-grants-2012_01
Patent number
US08101684B2

Reaction notes

Loading…