Water → 2,2-bis[N-(2-nitrophenyl)-{4-(4-aminophenoxy)phenyl}]hexafluoropropane

HRID 23973Notes

Reaction equation

HRID 23973 reaction equation
[NH2:1][C:2]1[CH:37]=[CH:36][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]([C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]4[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=4)=[CH:24][CH:23]=3)([C:18]([F:21])([F:20])[F:19])[C:14]([F:17])([F:16])[F:15])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.F[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[N+:45]([O-:47])=[O:46].[O-2:48].[Mg+2].[OH2:50]>C(OCC)(=O)C>[N+:45]([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=1[NH:35][C:32]1[CH:33]=[CH:34][C:29]([O:28][C:25]2[CH:26]=[CH:27][C:22]([C:13]([C:10]3[CH:11]=[CH:12][C:7]([O:6][C:5]4[CH:36]=[CH:37][C:2]([NH:1][C:3]5[CH:4]=[CH:5][CH:36]=[CH:37][C:2]=5[N+:1]([O-:50])=[O:48])=[CH:3][CH:4]=4)=[CH:8][CH:9]=3)([C:18]([F:19])([F:20])[F:21])[C:14]([F:16])([F:17])[F:15])=[CH:23][CH:24]=2)=[CH:30][CH:31]=1)([O-:47])=[O:46]

Participants

6

Reactant 4

HCID 962Water2×HCID 738951-Fluoro-2-nitrobenzeneHCID 94652Benzenamine, 4,4'-[[2,2,2-trifluoro-1-(trifluoromethyl)ethylidene]bis(4,1-phenyleneoxy)]bis-HCID 6850729Magnesium monoxide

Product 1

HCID 225712662,2-bis[N-(2-nitrophenyl)-{4-(4-aminophenoxy)phenyl}]hexafluoropropane

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

An autoclave was charged with 15 g (28.9 mmol) of 2,2-bis[4-(4-aminophenoxy)phenyl]hexafluoropropane, 7.62 ml (72.3 mmol) of o-fluoronitrobenzene, 6.5 g (161 mmol) of magnesium oxide and 75 ml of water, and the temperature of the autoclave was elevated to 250° C. with stirring. The reaction was continued for 12 hours at the same temperature. After the completion of the reaction, the system was cooled to the room temperature, and 800 ml of ethyl acetate and 300 ml of water were added thereto. Stirring was continued until the generated substance was dissolved in ethyl acetate. The obtained solution was filtered with cerite and extraction with ethyl acetate was conducted twice. Washing was carried out with 1N-hydrochloric acid, saturated aqueous solution of sodium hydrogen carbonate and then with saturated saline, followed by drying with absolute magnesium persulfate and the solvent was removed under reduced pressure. The resulting crude product was refined by using silica gel chromatography (hexane: ethyl acetate=5:1) and re-crystallized by using an ethanol-water mixed solution to obtain 15 g of 2,2-bis[N-(2-nitrophenyl)-{4-(4-aminophenoxy)phenyl}]hexafluoropropane in an orange crystal (yeild: 68%).

Workup

  1. customwas elevated to 250° C.
  2. customAfter the completion of the reaction
  3. additionwere added
  4. stirringStirring
  5. filtrationThe obtained solution was filtered with cerite and
  6. extractionextraction with ethyl acetate
  7. washWashing
  8. dry with materialby drying with absolute magnesium persulfate
  9. customthe solvent was removed under reduced pressure
  10. customre-crystallized

Sources & evidence

ORD record
ord-79a52cccc1504cf292bbdba8b84f27f0
Source dataset
uspto-grants-2005_02
Patent number
US06855774B2

Reaction notes

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