1,2-Dimethoxyethane → Ethyl [5-benzyloxy-4'-(trifluoromethyl)biphenyl-3-yl]acetate

Temperature

95 °C

A mixture of (3-benzyloxy-5-trifluoromethanesulfonyloxy-phenyl)-acetic acid ethyl ester (108 g, 0.26 mol), 4-(trifluoromethyl)phenylboronic acid (55.6 g, 0.29 mol), 1,2-dimethoxyethane (1.1 L) and aqueous Na2CO3 (2 M, 129 mL, 0.26 mol) was mechanically stirred while purging N2 at room temperature for 10 min. To this system was added Pd(Ph3)4 (480 mg, 0.42 mmol) and heated to reflux (95° C.) for 2.5 h. The red-brown mixture was diluted with EtOAc (0.5 L) and washed with saturated aqueous NaHCO3 solution (3×200 mL) and brine (2×200 mL). The organic fraction was dried (Na2SO4) and concentrated in vacuo. The crude mixture was purified by ISCO column chromatography to obtain (5-benzyloxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester (107 g, 100%).

1. customwhile purging N2 at room temperature for 10 min
2. temperatureheated
3. washwashed with saturated aqueous NaHCO3 solution (3×200 mL) and brine (2×200 mL)
4. dry with materialThe organic fraction was dried (Na2SO4)
5. concentrationconcentrated in vacuo
6. customThe crude mixture was purified by ISCO column chromatography

ORD record

ord-a8b352b1186e43a5b0c7be3109a891ea

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08247610B2