Fluorene → HCID 1957070, compound

HRID 1679158Notes

Reaction equation

HRID 1679158 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH:11]1[C:23]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]=2[CH:14]=[CH:13][CH:12]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([C:19]2[CH:18]=[CH:17][C:16]3[C:15]4[C:23](=[CH:11][CH:12]=[CH:13][CH:14]=4)[CH2:22][C:21]=3[CH:20]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6853FluoreneHCID 85014-Chlorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 1957070HCID 1957070, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

p-Chlorobenzoyl chloride (43.8 g.) was added dropwise to a stirred mixture of fluorene (41.5 g.) aluminum chloride (33.4 g.) and carbon disulphide (100 ml.). After the vigorous reaction had subsided the mixture was stirred and boiled under reflux for 6 hours. It was cooled, poured onto ice, the carbon disulphide distilled off on a steam bath, and the solid product filtered off, washed, dried and recrystallised from benzene to give 2-p-chlorobenzoylfluorene, m.p. 183° C. This was reacted by the method of Example 1 to give trans-1-(2-fluorenyl)-1-p-chlorophenyl-3-dimethylaminoprop-1-ene, hydrochloride from ethanol, m.p. 236°-237° C. Isomeric homogeneity was confirmed by n.m.r. spectroscopy.

Workup

  1. customAfter the vigorous reaction
  2. temperatureunder reflux for 6 hours
  3. temperatureIt was cooled
  4. additionpoured onto ice
  5. distillationthe carbon disulphide distilled off on a steam bath
  6. filtrationthe solid product filtered off
  7. washwashed
  8. customdried
  9. customrecrystallised from benzene

Sources & evidence

ORD record
ord-a9fbe9b2ba024e1a9b73f723f76922a4
Source dataset
uspto-grants-1978_03
Patent number
US04079081

Reaction notes

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