Ethyl 3-(2-Fluoro-4-hydroxyphenyl)propanoate synthesis
- Product Name:Ethyl 3-(2-Fluoro-4-hydroxyphenyl)propanoate
- CAS Number:691904-78-6
- Molecular formula:C11H13FO3
- Molecular Weight:212.22
691904-77-5
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691904-78-6
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Yield:691904-78-6 99.75%
Reaction Conditions:
Stage #1: 3-(2-fluoro-4-methoxyphenyl)propionic acid ethyl esterwith boron tribromide in dichloromethane at 0; for 0.5 h;
Stage #2: with ethanol in dichloromethane at 0;
Steps:
55
Intermediate 55: Ethyl 3-(2-fluoro-4-hydroxyphenyl) propanoateTo a 25 mL RB flask fitted with magnetic stirrer was charged with 10 mL of dichloromethane. To the stirred solvent was added ethyl 3-(2-fluoro-4-methoxyphenyl) propanoate (0.45 g, 2 mmol). The reaction mixture was cooled to 0 °C and boron tribromide (0.45 mL) was added drop wise. After stirred for 30 minutes, the reaction mixture was quenched with ethanol (1 mL) at 0 °C by slow addition. The reaction mixture was concentrated to distill off the solvent; ethyl acetate (10 mL) was added. The organic layer was washed with saturated NaHC03 solution (10 mL), followed by brine solution (10 mL). The organic layer was dried over anhydrous Na2S04 and the solvent was removed under reduced pressure. The product was obtained as colorless oil (0.421 g, yield: 99.75%). 1H NMR (300 MHz, CDCI3): δ 6.93-6.99(1, 1 H), 6.43-6.48(m, 2H), 5.54(s, 1H), 4.02-4.09(q, 2H), 2.79-2.85(t, 2H), 2.50-2.55(t, 2H), 1.14-1.19(t, 3H).
References:
WO2012/11125,2012,A1 Location in patent:Page/Page column 102-103
![2-Propenoic acid, 3-[2-fluoro-4-(phenylmethoxy)phenyl]-, ethyl ester](/CAS/20210305/GIF/729590-55-0.gif)
729590-55-0
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691904-78-6
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691904-78-6
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