[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([N+:11]([O-:13])=[O:12])[CH:7]=[CH:8][C:9]=1F.[CH3:14][C:15]1[O:19][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:17][C:16]=1[CH2:26][OH:27].Cl>CN(C)C=O>[F:3][C:4]1[CH:5]=[C:6]([N+:11]([O-:13])=[O:12])[CH:7]=[CH:8][C:9]=1[O:27][CH2:26][C:16]1[N:17]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:19][C:15]=1[CH3:14]
Sodium hydride (60% in oil, 2.2 g) was added portionwise, at 0° C., to a solution of 3,4-difluoronitrobenzene (8.8 g) and 5-methyl-2-phenyl-4-oxazolyl methanol (10.0 g) in N,N-dimethylformamide (DMF) (100 ml). The mixture was stirred for 3 hours at room temperature. The reaction mixture was poured into ice-water, which was acidified with 2N HCl. Then, resulting crystalline precipitate was collected by filtration, which was recrystallized from dichloromethane-methanol to give 3-fluoro-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)nitrobenzene (14.0 g, 81%) as colorless prisms, m.p.155-156° C.
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