Methyl 3-(2-fluorophenyl)propanoate synthesis
- Product Name:Methyl 3-(2-fluorophenyl)propanoate
- CAS Number:143654-59-5
- Molecular formula:C10H11FO2
- Molecular Weight:182.19
18944-77-9
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143654-59-5
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Yield:143654-59-5 100%
Reaction Conditions:
Stage #1: 2-fluorocinnamic acidwith hydrogen;palladium on activated charcoal in methanol;ethyl acetate; under 2585.81 Torr;
Stage #2: with diazomethane in diethyl ether;
Steps:
1.f f. Methyl 3-(2-fluorophenyl)propionate (1i)
In a Parr hydrogenation vessel is placed 2-fluorocinnamic acid (1h) (1.0 equiv) and palladium on carbon in a 1/1 methanol/ethyl acetate solution. The heterogeneous solution is placed on a Parr shaker and treated with hydrogen (50 psi) until uptake has ceased. The mixture is filtered through Celite and concentrated under reduced pressure. The residue is taken up in diethyl ether and is treated with diazomethane until the yellow color persists. The solution is concentrated under reduced pressure giving the crude methyl ester. Purification is effected by column chromatography on silica gel (hexane/ethyl acetate 5/1) to yield Methyl 3-(2-fluorophenyl)propionate (1i) in quantitative yield.
References:
US6410780,2002,B1 Location in patent:Page column 15
1643-26-1
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104201-65-2
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59845-58-8
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446-52-6
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