Fluorene → (2,4,6-Tri-isopropylphenylsulfonyl)fluorene

HRID 1709349

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.[CH:14]([C:17]1[CH:22]=[C:21]([CH:23]([CH3:25])[CH3:24])[CH:20]=[C:19]([CH:26]([CH3:28])[CH3:27])[C:18]=1[S:29](Cl)(=[O:31])=[O:30])([CH3:16])[CH3:15].[Cl-].[Al+3].[Cl-].[Cl-]>>[CH:14]([C:17]1[CH:22]=[C:21]([CH:23]([CH3:24])[CH3:25])[CH:20]=[C:19]([CH:26]([CH3:28])[CH3:27])[C:18]=1[S:29]([C: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)(=[O:31])=[O:30])([CH3:15])[CH3:16]

Participants

Reactant 3

HCID 6853Fluorene

HCID 810422,4,6-Tris(1-methylethyl)benzenesulfonyl chloride

HCID 6451240Aluminum(III) Chloride

Product 1

HCID 23037786(2,4,6-Tri-isopropylphenylsulfonyl)fluorene

Procedure

For example, fluorene can be reacted with 2,4,6-triisopropylbenzenesulfonyl chloride in the presence of aluminum chloride to yield 2 (2,4,6-tri-isopropylphenylsulfonyl)fluorene, which can be refluxed with sodium dichromate dihydrate in glacial acetic acid to yield 2 (2,4,6-triisopropylphenyl sulfonyl)fluorenone, which in turn can be refluxed with malononitrile in methanol in the presence of piperidine to yield 2 (2,4,6-triisopropylphenylsulfonyl)-9-(dicyanomethylene)fluorene.

Sources & evidence

ORD record: ord-fc2f5158bc814e009c0364ead3d93087
Source dataset: uspto-grants-1990_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04948911

Linked notes

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