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

HRID 1050654Notes

Reaction equation

HRID 1050654 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)fulvene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, a reaction vessel equipped with a dropping funnel was charged with 40 mL of dry tetrahydrofuran and 2.15 mL (25.89 mmol) of cyclopentadiene. While cooling this solution to 0° C., 18 mL (28.47 mmol) of a 1.58 mol/L hexane solution of n-butyllithium was slowly added dropwise and the mixture was stirred. Subsequently, a dropping funnel was charged with a solution prepared by dissolving 5.00 g (19.91 mmol) of 4,4′-dichlorobenzophenone in 30 mL of tetrahydrofuran, and the solution was slowly added dropwise. The mixture was left to be stand so that the temperature of the mixture was at room temperature, and stirred for one day. This reaction solution was then subjected to extraction with diethyl ether. The organic layer was washed with 1 N hydrochloric acid, a saturated aqueous solution of sodium hydrogen carbonate and saturated brine, and then dried over magnesium sulfate. The solvent was removed by distillation under reduce pressure. The residue was purified by using a silica gel column to obtain a target product (yield 3.37 g (57%)). The target product was identified by 1H-NMR.

Workup

  1. customUnder a nitrogen atmosphere, a reaction vessel equipped with a dropping funnel
  2. additionSubsequently, a dropping funnel was charged with a solution
  3. customprepared
  4. additionthe solution was slowly added dropwise
  5. waitThe mixture was left
  6. customwas at room temperature
  7. stirringstirred for one day
  8. extractionThis reaction solution was then subjected to extraction with diethyl ether
  9. washThe organic layer was washed with 1 N hydrochloric acid
  10. dry with materiala saturated aqueous solution of sodium hydrogen carbonate and saturated brine, and then dried over magnesium sulfate
  11. customThe solvent was removed by distillation
  12. customThe residue was purified
  13. customto obtain a target product (yield 3.37 g (57%))

Sources & evidence

ORD record
ord-992462ac7ecb46c29a2dc38de6b27d82
Source dataset
uspto-grants-2016_07
Patent number
US09382356B2

Reaction notes

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