Hydrochloric Acid → HCID 69275113, compound

Participants

Reaction Steps

An aqueous Na2CO3 solution (2M, 18.5 mL) is added to a stirred solution of (2-bromo-4-chloro-phenoxy)-acetic acid methyl ester (5.03 g, 18.0 mmol), phenylboronic acid (2.24 g, 18.4 mmol) and tetrakis(triphenylphosphine)palladium (0) (1.04 g, 0.900 mmol) in 1,4-dioxane (50 mL) at ambient temperature under argon. The resultant mixture is heated at 95° C. for 24 hours. At ambient temperature, 5N HCl (18.5 mL) is added to the mixture, followed by the addition of EtOAc (70 mL) and saturated aqueous NaCl solution (50 mL). The organic layer is separated, dried over MgSO4, filtered and concentrated. After chromatography on silica gel (CH2Cl2 followed by 0.5% HOAc/1% MeOH/98.5% CH2Cl2), 1.30 g (4.70 mmol, 26% yield) of the title compound and 2.41 g of the corresponding acid are obtained. The acid is dissolved in MeOH (5 mL)/CH2Cl2 (20 mL), and the solution is treated dropwise with (trimethylsilyl)diazomethane (2M in hexane, 8.8 mL). After stirring for 1 hour, the mixture is concentrated and chromatographed on silica gel (1:1 CH2Cl2/hexane) to give another 2.68 g of the title compound (9.68 mmol, 80% total yield) as oil. 1H NMR (CDCl3): δ3.77 (s, 3H), 4.58 (s, 2H), 6.80 (d, J=8.8 Hz, 1H), 7.21-7.26 (m, 1H), 7.33-7.37 (m, 2H), 7.42 (br t, J=7.4 Hz, 2H), 7.56 (d, J=6.9 Hz, 2H).

Provenance & Evidence