Bromobenzene → 2-Phenoxy-4-trifluoroacetylfluorobenzene

HRID 1588871Notes

Reaction equation

HRID 1588871 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]([F:13])([F:12])[F:11])=[O:9])=[CH:4][C:3]=1[O:14][CH3:15].C[Si](I)(C)C.[OH-].[Na+].Br[C:24]1[CH:29]=[CH:28]C=[CH:26][CH:25]=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]([F:13])([F:12])[F:11])=[O:9])=[CH:4][C:3]=1[O:14][C:15]1[CH:28]=[CH:29][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 4

HCID 7961BromobenzeneHCID 14798Sodium HydroxideHCID 85247Trimethylsilyl iodideHCID 197548242,2,2-Trifluoro-1-(4-fluoro-3-methoxyphenyl)ethanone

Product 1

HCID 199715862-Phenoxy-4-trifluoroacetylfluorobenzene

Procedure

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.

Sources & evidence

ORD record
ord-baa0fda7b0384dbcbe4e1ee24593098a
Source dataset
uspto-grants-1993_06
Patent number
US05223536

Reaction notes

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