1,3-Isobenzofurandione, 5-fluoro- → 9,9-Bis{4-(4-fluorophthalimido)phenyl}fluorene

HRID 129951Notes

Reaction equation

HRID 129951 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:21]3[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=3)[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][CH:13]=3)=[CH:4][CH:3]=1.[F:28][C:29]1[CH:30]=[C:31]2[C:36](=[O:37])O[C:33](=[O:34])[C:32]2=[CH:38][CH:39]=1>C(O)(=O)C>[F:28][C:29]1[CH:30]=[C:31]2[C:36](=[O:37])[N:1]([C:2]3[CH:3]=[CH:4][C:5]([C:8]4([C:21]5[CH:22]=[CH:23][C:24]([N:27]6[C:36](=[O:37])[C:31]7=[CH:30][C:29]([F:28])=[CH:39][CH:38]=[C:32]7[C:33]6=[O:34])=[CH:25][CH:26]=5)[C:9]5[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=5[C:15]5[C:20]4=[CH:19][CH:18]=[CH:17][CH:16]=5)=[CH:6][CH:7]=3)[C:33](=[O:34])[C:32]2=[CH:38][CH:39]=1

Participants

4

Reactant 2

HCID 675721,3-Isobenzofurandione, 5-fluoro-HCID 6315524,4'-(9-Fluorenylidene)dianiline

Product 1

HCID 153007029,9-Bis{4-(4-fluorophthalimido)phenyl}fluorene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 9,9-bis(4-aminophenyl)fluorene (17.4 g, 50 mmol), 4-fluorophthalic anhydride (18.3 g, 110 mmol), and 250 ml of acetic acid was stirred and heated under reflux for five hours and then stirred at ambient temperature overnight. A colorless precipitate formed which was filtered, washed twice with 150 ml of ethanol, washed twice with 100 ml of hexane, suction-dried for two hours, and then dried in a vacuum oven at 120° C. for 16 hours. The title compound was isolated as a colorless powder (29.2 g, 90.6% yield) that had melting point of 323.5°-326° C. and a 1H NMR spectrum (DMSO-d6) corresponding to δ8.02 (m, 4H), 7.86 (dd, 2H), 7.72 (m, 2H), 7.60 (d, 2H), 7.46 (t, 2H), and 7.35 (m, 10H).

Workup

  1. temperatureheated
  2. temperatureunder reflux for five hours
  3. stirringstirred at ambient temperature overnight
  4. customA colorless precipitate formed which
  5. filtrationwas filtered
  6. washwashed twice with 150 ml of ethanol
  7. washwashed twice with 100 ml of hexane
  8. customsuction-dried for two hours
  9. customdried in a vacuum oven at 120° C. for 16 hours

Sources & evidence

ORD record
ord-e6482dda70044c6f9f5c39f6444f0770
Source dataset
uspto-grants-1995_11
Patent number
US05470987

Reaction notes

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