1-Chloro-2,4-Dinitrobenzene → 2,4-Dinitro-1-(2,2,2-trifluoroethoxy)benzene
Reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[F:14][C:15]([F:19])([F:18])[CH2:16][O-:17]>>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([O:17][CH2:16][C:15]([F:19])([F:18])[F:14])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=1)([O-:10])=[O:9]Participants
Procedure
In a first reaction step, 1-chloro-2,4-dinitrobenzene (II) is reacted with 2,2,2-trifluoroethanolate to form 1,3-dinitro-4-(2',2',2'-trifluoroethoxy)-benzene (III) according to the following reaction: ##STR2## For obtaining this reaction, 4.0 g (0.17 mole) sodium is completely dissolved in 100 ml 2,2,2-trifluoroethanol. Thereafter, 21.5 g (0.11 mole) of finely powdered 1-chloro-2,4-dinitrobenzene is added to the solution. The mixture is then heated under reflux for 3 hours and the excessive trifluoroethanol is distilled off under normal pressure. The remaining oil is dissolved in 210 ml ethanol. Through addition of 170 ml water, the reaction product III is precipitated in a crystalline form. It is sucked off, washed with a water-ethanol mixture (1:1) and then dried over CaCl2. The yield of 1,3-dinitro-4-(2',2',2'-trifluoroethoxy)-benzene is 27.0 g (0.1 mole 95% relative to the use 1-chloro-2,4-dinitrobenzene). The substance has a melting point of 76°-77° C.
Sources & evidence
- ORD record
- ord-3cdb5d03a8e44970bdd7b65ae2a0fe6c
- Source dataset
- uspto-grants-1985_09
- Patent number
- US04543425
Reaction notes
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