Benzeneacetic acid, 4-chloro-α-methylene-, ethyl ester synthesis
- Product Name:Benzeneacetic acid, 4-chloro-α-methylene-, ethyl ester
- CAS Number:101492-44-8
- Molecular formula:C11H11ClO2
- Molecular Weight:210.66
Yield:101492-44-8 41 %
Reaction Conditions:
with (bis(tricyclohexyl)phosphine)palladium(II) dichloride;water;potassium acetate in o-xylene at 90;Schlenk technique;Inert atmosphere;
Steps:
6. General procedure
General procedure: Arylboronic acid (0.40 mmol, 2.0 equiv), potassium acetate (0.60 mmol, 3.0 equiv) were placed in a transparent Schlenk tube equipped with a stirring bar. The tube kept in vacuum then flushed with argon. This procedure was repeated for 3-4 times. Alkyne (0.20 mmol, 1.0 equiv), Pd(PCy3)2Cl2 (400 ppm) and the solvent (o-xylene, 3.0 mL, H2O, 1.0 mL) was added under Ar atmosphere. The reaction mixture was stirred at 90 oC for 12 h (oil bath). The reaction mixture was cooled to room temperature, then extracted with ethyl acetate. The organic layers were combined and dried over Na2SO4, then concentrated under vacuo. The product was purified by flash column chromatography on silica gel (petrol ether/ethyl acetate). Pd(PCy3)2Cl2 (400 ppm catalyst for 0.2 mmol reaction) : dissolve Pd(PCy3)2Cl2 (3 mg, 0.02 equiv ) in 10 mL o-xylene, and then take 200 μL of the solution.
References:
Xu, Lei;Li, Shiyu;Zhang, Qi;Deng, Ning;Zhang, Biao;Xu, Huajian [Chinese Chemical Letters,2023,vol. 34,# 2,art. no. 107534] Location in patent:supporting information
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