1-Benzyloxy-4-nitro-2,3,5,6-tetrafluorobenzene → 1-Benzyloxy-3-(prop-2-enyloxy)-4-nitro-2,5,6-trifluorobenzene
Reaction equation
[CH2:1]([O:8][C:9]1[C:14]([F:15])=[C:13](F)[C:12]([N+:17]([O-:19])=[O:18])=[C:11]([F:20])[C:10]=1[F:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22]([O-:25])[CH:23]=[CH2:24].[Na+]>C(#N)C>[CH2:1]([O:8][C:9]1[C:10]([F:21])=[C:11]([F:20])[C:12]([N+:17]([O-:19])=[O:18])=[C:13]([O:25][CH2:22][CH:23]=[CH2:24])[C:14]=1[F:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
30.1 g of the 1-benzyloxy-4-nitro-2,3,5,6-tetra-fluorobenzene prepared as described in Example 4 (0.1 mol) are dissolved in 250 ml of dry acetonitrile in a three-neck flask fitted with reflux condenser and stirrer, and 8 g of sodium prop-2-enolate (0.1 mol) are added in portions to the solution. The reaction mixture is stirred at room temperature for 1 hour and then refluxed for 24 hours. The reaction solution is then filtered via a fluted filter, and the crude product is extracted by shaking with 150 ml of ethyl acetate and 300 ml of water. The organic phase is washed three times with water, dried over sodium sulfate and evaporated to half in a rotary evaporator. The precipitated reaction product is then recrystallized from a mixture of n-hexane and methylene chloride (volume ratio 1:1) and then dried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum drying cabinet.