Fluorene → 1,1'-(9H-Fluorene-2,7-diyl)bis(4-chlorobutan-1-one)

HRID 1576961Notes

Reaction equation

HRID 1576961 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.[Cl:14][CH2:15][CH2:16][CH2:17][C:18](Cl)=[O:19].[Cl-:21].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[Cl:14][CH2:15][CH2:16][CH2:17][C:18]([C:9]1[CH:8]=[CH:7][C:6]2[C:5]3[C:13](=[CH:1][C:2]([C:18](=[O:19])[CH2:17][CH2:16][CH2:15][Cl:21])=[CH:3][CH:4]=3)[CH2:12][C:11]=2[CH:10]=1)=[O:19]

Participants

5

Reactant 3

HCID 6853FluoreneHCID 783704-Chlorobutyryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 131705491,1'-(9H-Fluorene-2,7-diyl)bis(4-chlorobutan-1-one)

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 23.6 g (0.142 mole) of fluorene and 50.0 g (0.35 mole) of 4-chlorobutyryl chloride in 1500 ml of methylene chloride chilled to -20°C., is added 39.8 g (0.298 mole) of aluminum chloride with rapid stirring. The reaction mixture is refluxed for 4 hours, stirred at room temperature for 16 hours and is poured onto an ice/concentrated HCl mixture. The organic layer is separated, washed with saturated sodium bicarbonate solution and dried over magnesium sulfate. The methylene chloride solution is filtered, evaporated to dryness, and the solid residue recrystallized from acetone to yield the desired 2,7-bis(4-chlorobutyryl)fluorene.

Workup

  1. temperatureThe reaction mixture is refluxed for 4 hours
  2. customThe organic layer is separated
  3. washwashed with saturated sodium bicarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe methylene chloride solution is filtered
  6. customevaporated to dryness
  7. customthe solid residue recrystallized from acetone

Sources & evidence

ORD record
ord-c91369645a564efe9be4e88ea10e37fd
Source dataset
uspto-grants-1976_09
Patent number
US03983124

Reaction notes

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