methyl 3-ethylbenzoate synthesis
- Product Name:methyl 3-ethylbenzoate
- CAS Number:50604-00-7
- Molecular formula:C10H12O2
- Molecular Weight:164.2
Yield:50604-00-7 96%
Reaction Conditions:
with potassium phosphate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 in tetrahydrofuran;hexane;water;Reflux;
Steps:
78.a a) Methyl 3-ethylbenzoate
Methyl 3-bromobenzoate (1.00 g, 4.65 mmol, 1 equiv.) and [1,1’-bi s(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (PdC12(dppf)CH2C12, 95 mg, 0.12 mmol, 2.5 mol%) were dissolved in tetrahydrofuran (10 mL). K3P04 (4.65 mL, 2.0 M in water, 9.30 mmol, 2 equiv.) was thereafter added followed by triethylborane (4.65 mL, 1.0 M in hexanes, 4.65 mmol, 1 equiv.) and the mixture washeated to reflux. After stirring at reflux overnight the reaction mixture was allowed to reach room temperature and the solid was filtered off. To the solution was added ethyl acetate andwater and the product was extracted with ethyl acetate (x2). The combined organic phases were dried over sodim sulfate and the solvent was removed under reduced pressure. The product was purified by column chromatography (heptane/ethyl acetate 19:1) to give 733 mg (96%) of the product. MS (ESIj: m/z 165 [M+H].
References:
WO2017/9651,2017,A1 Location in patent:Page/Page column 123; 124
