Potassium Phosphate, Tribasic → HCID 68686708, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl (2-bromophenyl)acetate of Step A (20.0 g, 87.3 mmol), 4-carboxybenzeneboronic acid (14.5 g, 87.4 mmol), [1,1′-bis(diphenylphosphino) ferrocene]dichloropalladium [II] (3.6 g, 4.4 mmol) and potassium phosphate (55.6 g, 262 mmol) in dry 4-dioxane (ca. 400 mL) was heated at 100° C. with vigorous stirring for 17 hours. The cooled mixture was then filtered through Celite and washed with 1,4-dioxane (ca. 200 mL). The filtrate was concentrated in vacuo to give a tacky brown solid (28.0 g). Purification by flash chromatography using a solvent gradient of 320:1:1 to 80:1:1 dichloromethane/acetic acid/methanol afforded an impure tacky orange solid (11.9 g). The solid product was dissolved in ethyl acetate (300 mL), filtered from insoluble material, and the filtrate washed with water (2×150 mL) and brine (150 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to give a light orange solid (7.3 g). Recrystallization from diethyl ether provided the title compound (5.2 g, 22%) as pale orange needles.

Provenance & Evidence