[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][CH2:10][CH2:11][N:12]=1>O.OO.[Ni].C1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][CH:10]=[CH:11][N:12]=1A mixture of 2-fluoro-1-(4,5-dihydrooxazol-2-yl)benzene (4.5 g, 27.3 mmol), nickel peroxide hydrate (7 g) and benzene (40 mL) was heated 24 hours at reflux. The reaction mixture was allowed to cool to 25° C., then filtered and concentrated by rotary evaporation. The residue was purified on silica gel by column chromatography eluting with hexanes/ethyl acetate (5:1) to give 2-fluoro-1-oxazol-2-ylbenzene (0.5 g, 3.07 mmol).
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