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

HRID 1770295Notes

Reaction equation

HRID 1770295 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-a449b3f95269440b93c44d24a1295dc5
Source dataset
uspto-grants-1995_01
Patent number
US05386002

Reaction notes

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