3-Nitrophenol → 1,3-Bis(3-nitrophenoxy)-5-trifluoromethylbenzene

HRID 1603980Notes

Reaction equation

[N+]([C:4]1[CH:5]=[C:6]([C:13]([F:16])([F:15])[F:14])[CH:7]=[C:8]([N+]([O-])=O)[CH:9]=1)([O-])=O.[N+:17]([C:20]1[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=1)([O-:19])=[O:18]>>[N+:17]([C:20]1[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=1)[O:26][C:8]1[CH:7]=[C:6]([C:13]([F:14])([F:15])[F:16])[CH:5]=[C:4]([O:26][C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([N+:17]([O-:19])=[O:18])[CH:21]=2)[CH:9]=1)([O-:19])=[O:18]

Participants

Reactant 2

HCID 111373-Nitrophenol

HCID 123060alpha,alpha,alpha-Trifluoro-3,5-dinitrotoluene

Product 1

HCID 186924191,3-Bis(3-nitrophenoxy)-5-trifluoromethylbenzene

Procedure

In an example of the process (i), 3,5-dinitrobenzotrifluoride is condensed with m-nitrophenol in the presence of a base, in an aprotic solvent, to give 1,3-bis(3-nitrophenoxy)-5-trifluoromethylbenzene, which is then reduced to 1,3-bis(3-aminophenoxy)-5-trifluoromethylbenzene, in a high yield.

Sources & evidence

ORD record: ord-ee4172a1995349b9b5d718dd7832b325
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05990261

Reaction notes

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