Aniline → Fluorene

HRID 1290015Notes

Reaction equation

HRID 1290015 reaction equation
C[C:2]1[CH:7]=[C:6](N)[C:5]([CH3:9])=[CH:4][C:3]=1N.N[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH:13]1[C:14]2[CH2:15][C:6]3[C:5](=[CH:4][CH:3]=[CH:2][CH:7]=3)[C:9]=2[CH:16]=[CH:17][CH:12]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 1608242,5-Dimethyl-p-phenylenediamine

Product 1

HCID 6853Fluorene

Procedure

In the following Examples, 9,9-bis(3-methyl-4-aminophenyl)fluorene (OTBAF) was prepared as described in U.S. Pat. No. 4,684,678, Example 2. It was recrystallized from anhydrous dichloroethane prior to use. p-Phenylenediamine (PDA) was obtained in a sublimed, zone-refined form from Aldrich Chemical Company. 2,5-Dimethyl(p-phenylenediamine) (DMPDA) was obtained from Aldrich and recrystallized from absolute ethanol prior to use. 4,4'-(1,4-Phenylenebis(1-methylethylidene)) bisbenzamine (EHBPT) was obtained from Shell Chemical Company and was recrystallized from anhydrous dichloroethane prior to use. 9,9-Bis((3,5-dimethyl-4-amino)phenyl)fluorene (DM-OTBAF),9,9-Bis[(3-ethyl-5-methyl-4-amino)phenyl)]fluorene (DE-OTBAF), and 9,9-bis[(2,5-diethyl-4-amino)phenyl]fluorene (DEAF) were prepared analogously, but using a different aniline derivative, as OTBAF, and were recrystallized prior to use. 3,3'-4,4'-Benzophenone tetracarboxylic acid dianhydride (BTDA) was purchased from Aldrich in a sublimed form. 4,4'-Oxydi(phthalic anhydride) (ODPA) was obtained from Occidental Chemical Company and purified via recrystallization from anisole. Pyromellitic dianhydride (PMDA), 2,2'-bis-((3,4-dicarboxyphenyl)-hexafluoropropane dianhydride (6FDA), 3,3'-4,4'-biphenyltetracarboxylic dianhydride (s-BPDA), and DSDA (3,3'-4,4'-diphenyl sulfone tetracarboxylic acid dianhydride) were purchased and used as received from Chriskev Company of Leawood, Kansas.

Workup

  1. customrecrystallized from absolute ethanol
  2. customwas recrystallized from anhydrous dichloroethane
  3. customas OTBAF, and were recrystallized
  4. custompurified via recrystallization from anisole

Sources & evidence

ORD record
ord-c6f7dfac400a440d84e7e78c2c11ba91
Source dataset
uspto-grants-1998_05
Patent number
US05750641

Reaction notes

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