[Na].F[C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.O.[F:13][C:14]([F:18])([F:17])[CH2:15][OH:16]>>[F:13][C:14]([F:18])([F:17])[CH2:15][O:16][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1Under a nitrogen atmosphere, 10.1 g (0.44 mol) of sodium was dissolved in 200 ml of 2,2,2-trifluoro ethanol in 300 ml of a three-necked flask, to which 40 ml (0.38 mol) of p-fluoronitro benzene was dropped and refluxed for 4 hours. After cooling to a room temperature, water was poured (about 1 liter), and precipitated solids were washed with water and dried, to obtain p-(2,2,2-trifluoroethoxy) nitrobenzene (yield: 62%; and melting point: 76.5° C.).
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