Dinitrofluorobenzene → 4-[6-(2,4-Dinitrophenoxy)-2,2,3,3,4,4,5,5-octafluorohexyloxy]-2,3,5,6-tetrafluorobenzonitrile
Reaction equation
[F:1][C:2]([F:16])([C:5]([F:15])([F:14])[C:6]([F:13])([F:12])[C:7]([F:11])([F:10])[CH2:8][OH:9])[CH2:3][OH:4].F[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:19]=1[N+:27]([O-:29])=[O:28].C(N(CC)CC)C.[F:37][C:38]1[C:43]([C:44]#[N:45])=[C:42]([F:46])[C:41]([F:47])=[C:40](F)[C:39]=1[F:49]>CC(C)=O>[N+:27]([C:19]1[CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=[CH:23][C:18]=1[O:9][CH2:8][C:7]([F:10])([F:11])[C:6]([F:13])([F:12])[C:5]([F:14])([F:15])[C:2]([F:16])([F:1])[CH2:3][O:4][C:40]1[C:39]([F:49])=[C:38]([F:37])[C:43]([C:44]#[N:45])=[C:42]([F:46])[C:41]=1[F:47])([O-:29])=[O:28]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 2,2,3,3,4,4,5,5-octafluoro-1,6-hexanediol (78.63 g, 0.3 mol, Aldrich Chemical Co., Milwaukee, Wis.), 1-fluoro-2,4-dinitrobenzene (18.6 g, 0.10 mmol), triethyl amine (42 mL, 0.3 mol) and acetone (100 mL) was heated to 80° C. for 1.5 hr. After aqueous workup the excess hexanediol removed by Kugelrohr distillation and the dimer by-product was removed by crystallization. The residual oil was treated with pentafluorobenzonitrile (19.3 g, 0.10 mol), triethyl amine (15.3 mL, 0.11 mol) and acetone (100 mL) and heated to reflux for 4 h. Aqueous workup followed by extraction gave 4-[6-(2,4-dinitrophenoxy)-2,2,3,3,4,4,5,5-octafluorohexyloxy]-2,3,5,6-tetrafluorobenzonitrile as an orange oil.
Workup
- customAfter aqueous workup the excess hexanediol removed by Kugelrohr distillation
- customthe dimer by-product was removed by crystallization
- temperatureheated
- temperatureto reflux for 4 h
- extractionAqueous workup followed by extraction
Sources & evidence
- ORD record
- ord-02fa623560f343dda700396974cded81
- Source dataset
- uspto-grants-1999_09
- Patent number
- US05958293
Reaction notes
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