Bromide ion → 4-Bromo-3-(trifluoromethoxy)benzaldehyde
反応式
[O:1]1CCO[CH:2]1[C:6]1[CH:12]=[CH:11][C:9](N)=[C:8]([O:13][C:14]([F:17])([F:16])[F:15])[CH:7]=1.[Br-:18]>>[Br:18][C:9]1[CH:11]=[CH:12][C:6]([CH:2]=[O:1])=[CH:7][C:8]=1[O:13][C:14]([F:17])([F:16])[F:15]参加物
実験手順
In Scheme 31 are shown 2 methods that may be used for the synthesis of 4-bromo-3-(trifluoromethoxy)benzaldehyde or 4-chloro-3-(trifluoromethoxy)benzaldehyde. Method 1: Commercially available 4-amino-3-(trifluoromethoxy)benzoic acid can be converted into the ester followed by a Sandmeyer reaction, described in Scheme 30, to provide the bromide or chloride. Reduction of the ester provides 4-bromo-3-(trifluoromethoxy)benzyl alcohol. The alcohol can be oxidized to the aldehyde to give the desired substituted benzaldehyde. Method 2: Commercially available 4-bromo-2-(trifluoromethoxy)aniline can be protected on the amino group with a suitable amino protecting groups well known to those skilled in the art of organic chemistry. The bromine can then be converted to the lithio or magnesio derivative and reacted directly with dimethylformamide to provide the 4-aminoprotected-3-(trifluoromethoxy)benzaldehyde derivative. Removal of the N-protecting group followed by protection of the aldehyde provides 4-(1,3-dioxolan-2-yl)-2-(trifluoromethoxy)aniline. Conversion of the amine to a bromide via the Sandmeyer method of Scheme 30 followed by hydrolysis of the dioxolane provides 4-bromo-3-(trifluoromethoxy)benzaldehyde.
出典と根拠
- ORDレコード
- ord-21f04d8df2de441e96b0ce1560073f9b
- 出典データセット
- uspto-grants-2003_07
- 特許番号
- US06593335B1
反応ノート
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