2-(2-fluoro[1,1'-biphenyl]-4-yl)acetic acid -Drug Synthesis Database

【结构式】

【分子编号】34113

【品名】2-(2-fluoro[1,1'-biphenyl]-4-yl)acetic acid

【CA登记号】

【分子式】C₁₄H₁₁FO₂

【分子量】230.2385432

【元素组成】C 73.03% H 4.82% F 8.25% O 13.9%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(VII)

By reaction of ethyl 2-fluoro-4-biphenylylacetate (I) first with diethyl carbonate and sodium ethoxide, and then with dimethyl sulfate in ethanol to give diethyl 2-fluoro-4-biphenylyl-alpha-methylmalonate (II), which was hydrolyzed with NaOH in ethanol and finally decarboxylated at 180-200 C. The starting product (I) was obtained as follows: the Ullman condensation of 4-bromo-3-nitroacetophenone (III) gives 2-nitro-4-acetylbiphenyl (IV), which was reduced to the corresponding amino compound (V). This, by the Schieman reaction was converted into 2-fluoro-4-acetylbiphenyl (VI), which by heating with sulfur and morpholine (B) gave 2-fluoro-4-biphenylylacetic acid (VII), and finally (VII) was esterified by refluxing with ethanol and H2SO4.

参考文献中间体

合成目标

【1】 Adams, S.S.; et al.; 2-(Mono- and difluoro-4-biphenyl)propionic acids. US 3755427 .
【2】 Thorpe, P.; Castaner, J.; Flurbiprofen. Drugs Fut 1976, 1, 7, 323.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(B)	10388	Morpholine	110-91-8	C₄H₉NO	详情	详情
(A)	13364	Benzene	71-43-2	C₆H₆	详情	详情
(I)	34107	ethyl 2-(2-fluoro[1,1'-biphenyl]-4-yl)acetate		C₁₆H₁₅FO₂	详情	详情
(II)	34108	diethyl 2-(2-fluoro[1,1'-biphenyl]-4-yl)-2-methylmalonate		C₂₀H₂₁FO₄	详情	详情
(III)	34109	1-(4-bromo-3-nitrophenyl)-1-ethanone	18640-58-9	C₈H₆BrNO₃	详情	详情
(IV)	34110	1-(2-nitro[1,1'-biphenyl]-4-yl)-1-ethanone		C₁₄H₁₁NO₃	详情	详情
(V)	34111	1-(2-amino[1,1'-biphenyl]-4-yl)-1-ethanone		C₁₄H₁₃NO	详情	详情
(VI)	34112	1-(2-fluoro[1,1'-biphenyl]-4-yl)-1-ethanone		C₁₄H₁₁FO	详情	详情
(VII)	34113	2-(2-fluoro[1,1'-biphenyl]-4-yl)acetic acid		C₁₄H₁₁FO₂	详情	详情

Extended Information