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a) Sulfuric acid (0.484 ml, 9.08 mmol) was added dropwise to a solution of 2-(4-(trifluoromethoxy)phenyl)acetic acid (2.0 g, 9.08 mmol) in ethanol (20 ml), and heated under reflux for 5 hours. The reaction mixture was concentrated in vacuo, diluted with ethyl acetate (100 ml), washed with saturated NaHCO3 solution and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate/hexane: 0/100 to 20/80) to give ethyl 2-(4-(trifluoromethoxy)phenyl)acetate (2.06 g, yield 91percent) as yellow oil.
a) Sulfuric acid (0.484 ml, 9.08 mmol) was added dropwise to a solution of 2-(4-(trifluoromethoxy)phenyl)acetic acid (2.0 g, 9.08 mmol) in ethanol (20 ml), and heated under reflux for 5 hours. The reaction mixture was concentrated in vacuo, diluted with ethyl acetate (100 ml), washed with saturated NaHCO3 solution and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate/hexane: 0/100 to 20/80) to give ethyl 2-(4-(trifluoromethoxy)phenyl)acetate (2.06 g, yield 91%) as yellow oil.
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 5.0h;
b) A mixture of <strong>[1206550-93-7]ethyl 2-(4-(trifluoromethoxy)phenyl)acetate</strong> (1.99 g, 8.00 mmol), N-bromosuccinimide (NBS) (1.57 g, 8.80 mmol) and 2,2'-azobis(2-methylpropionitrile) (AIBN) (66 mg, 0.400 mmol) in carbon tetrachloride (10 ml) was heated under reflux for 5 hours. The reaction mixture was concentrated in vacuo, diluted with diethyl ether (200 ml), washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo to give ethyl 2-bromo-2-(4-(trifluoromethoxy)phenyl)acetate (65) (2.70 g, quantitative yield) as yellow oil.
With copper(II) bis(trifluoromethanesulfonate); triethylamine; In N,N-dimethyl acetamide; at 20.0℃;Sealed tube;
General procedure: General Procedure A: Cu(OTf)2 (54.3 mg, 0.150 mmol, 0.30 equiv.) and arylboronic ester (1.00 mmol, 1.20 to 2.00 equiv.) were added sequentially to a 1 dram vial charged with a stirbar. The carboxylic acid (0.500 mmol, 1.00 equiv.) was added as a solution in anhydrous DMA (0.6 mL). Additional DMA (2×0.3 mL) was used to quantitatively transfer the solution to the reaction mixture. The solution was stirred until a homogeneous pale blue solution was formed (approximately 2 minutes, partially heterogeneous mixtures obtained when using increased Cu loadings), followed by the addition of triethylamine (0.42 mL, 3.0 mmol, 6.0 equiv.). The vial was sealed with a PTFE-lined cap, exposed to air via a needle, and gently stirred at room temperature. Upon completion of the reaction (24 to 72 h), the reaction mixture was diluted with EtOAc (40 mL), and washed sequentially with NH4Cl (15 mL), 0.5 M NaOH (2×20 mL), and brine (15 mL). The organic layer was dried with Na2SO4, concentrated in vacuo, and purified by silica gel chromatography. No difference was observed if reactions were prepared in an atmosphere-controlled glovebox, then exposed to ambient air.
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