Hypofluorous acid, trifluoromethyl ester → 1-(3-Fluoro-2,6-dimethoxyphenyl)propan-1-one
반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[C:11](=[O:14])[CH2:12][CH3:13].[F:15]OC(F)(F)F>>[F:15][C:8]1[C:3]([O:2][CH3:1])=[C:4]([C:11](=[O:14])[CH2:12][CH3:13])[C:5]([O:9][CH3:10])=[CH:6][CH:7]=1참가 물질
실험 절차
The electrophilic fluorination of compound IV can be performed by passing trifluoromethyl hypofluorite into a stirred mixture of the compound in Freon at -78° C. The reaction is monitored frequently by thin layer chromatography to avoid over-fluorination. The crude product from the reaction is purified by column chromatography to provide 1-(3-fluoro-2,6-dimethoxyphenyl)propan-1-one V which is then reduced with borane in the presence of boron trifluoride in boiling tetrahydrofuran to give 1-fluoro-2,4-dimethoxy-3-propylbenzene VI in excellent yield. Acylation of V with an alkanoyl chloride under conventional Friedel-Crafts, conditions provides a compound of general structure VII which on treatment with boron tribromide in methylene chloride at -78° C. is demethylated to yield the afore-mentioned 1-(2,4-dihydroxy-5-fluoro-3-propylphenyl)alkan-1-one of general formula VIII.
후처리
- additioninto a stirred mixture of the compound in Freon at -78° C
- customThe crude product from the reaction is purified by column chromatography
출처 및 근거
- ORD 기록
- ord-b51b82a441a34e23b8fe5bc08245314a
- 출처 데이터셋
- uspto-grants-1990_03
- 특허 번호
- US04906658
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