2,2,2-Trifluoro-N-methoxy-N-methylacetamide → 2,2,2-Trifluoro-1-(4-fluoro-3-methoxyphenyl)ethanone

반응식

Br[C:2]1[C:3]([F:10])=[C:4]([O:8][CH3:9])[CH:5]=[CH:6][CH:7]=1.BrC1C=CC(F)=C(OC)C=1.CON(C)[C:24](=[O:29])[C:25]([F:28])([F:27])[F:26]>O1CCCC1>[F:10][C:3]1[CH:2]=[CH:7][C:6]([C:24]([C:25]([F:28])([F:27])[F:26])=[O:29])=[CH:5][C:4]=1[O:8][CH3:9]

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실험 절차

Trifluoromethyl 4-fluoro-3-phenoxyphenyl ketone may be prepared using the following procedure. Bromination of 2-fluoroanisole yields a mixture of bromo-2-fluoroanisole isomers from which 5-bromo-2-fluoroanisole is isolated. The Grignard reagent of 5-bromo-2-fluoroanisole is then prepared and is in turn reacted with N-methoxy-N-methyl-2,2,2-trifluoroacetamide in tetrahydrofuran, yielding trifluoromethyl 4-fluoro-3-methoxyphenyl ketone. This ketone is protected by formation of the corresponding ketal, which is in turn treated with trimethylsilyl iodide, sodium hydroxide, bromobenzene, and acid, yielding trifluoromethyl (4-fluoro-3-phenoxyphenyl) ketone.