Potassium Carbonate → HCID 22601714, compound

Participants

Reaction Conditions

Reaction Steps

2-(3-Bromo-5-iodo-4-methylthien-2-yl)-1,3-dioxolane (12.4 g, 33.1 mmol), 4-methoxyphenylboronic acid (5.5 g, 36 mmol), K2CO3 (15 g, 110 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium [II] (1.3 g, 1.6 mmol) were combined in 20% aqueous dimethoxyethane (130 mL) and heated at 75° C. After 3 h, the cooled mixture was filtered through Celite and washed with ethyl acetate (350 mL). The filtrate was washed with 1 N aqueous NaOH and brine (350 mL each), dried (K2CO3) and concentrated in vacuo to give the crude product (13.1 g) as a dark solid which was pre-adsorbed on silica gel (40 g). Flash chromatography (600 g silica, gradient 2.5%-5% ethyl acetate-hexane) gave the title compound (9.5 g, 81%, m.p. 103-04° C.) as a white crystalline solid.

Provenance & Evidence