Benzophenone → 9-(Diphenylmethylidene)-9H-fluorene

HRID 2282790Notes

Reaction equation

HRID 2282790 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].[C:20]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Cl-].[NH4+]>C(OCC)C.O1CCCC1>[C:21]1([C:20]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[C:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 3102BenzophenoneHCID 6853FluoreneHCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 2388729-(Diphenylmethylidene)-9H-fluoreneYield 36.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dry tetrahydrofuran (500 ml) was added to a mixture of fluorene (10.00 g, 60.16 mmoles) and potassium tert-butoxide (7.43 g, 66.18 mmoles) under nitrogen and stirred at room temperature for 5 minutes. Benzophenone (10.96 g, 60.16 mmoles) was then added as a solid and the reaction mixture was stirred for a further 20 hours under nitrogen at room temperature. Aqueous ammonium chloride (sat., 200 ml) was then added and stirred until the colour had faded. Diethyl ether (100 ml) was added and the aqueous layer separated and extracted with diethyl ether (2×100 ml). The combined organic layers were washed with water (3×200 ml), dried over anhydrous magnesium sulfate and evaporated. The crude product (16.0 g) was recrystallised twice from dichloromethane:hexane (100:200 ml) and then from dichloromethane:acetonitrile (100:200 ml) and then dried under vacuum to give white crystals of 9-(diphenylmethylene)-9H-fluorene (7.34 g).

Workup

  1. stirringthe reaction mixture was stirred for a further 20 hours under nitrogen at room temperature
  2. stirringstirred until the colour
  3. customthe aqueous layer separated
  4. extractionextracted with diethyl ether (2×100 ml)
  5. washThe combined organic layers were washed with water (3×200 ml)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated
  8. customThe crude product (16.0 g) was recrystallised twice from dichloromethane
  9. dry with materialhexane (100:200 ml) and then from dichloromethane:acetonitrile (100:200 ml) and then dried under vacuum

Sources & evidence

ORD record
ord-e2244f6c24204aaa8ca6e7099f99270c
Source dataset
uspto-grants-2015_09
Patent number
US09142782B2

Reaction notes

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