1,2-Dimethoxyethane → 2-Bromo-4-(4-fluoro-benzyl)-1-methoxy-benzene

Participants

Reaction Conditions

Reaction Steps

In a 250 mL round-bottomed flask equipped with a stir bar was placed 3-bromo-4-methoxybenzyl bromide (5.0 g, 17.9 mmol), 4-fluorophenylboronic acid (2.76 g, 19.7 mmol), potassium phosphate (tribasic) (7.60 g, 35.8 mmol), dimethoxyethane (30 mL) and 50% aqueous ethanol (30 mL). The mixture was degassed with nitrogen for 30 minutes and then added tetrakis(triphenylphosphine)palladium(0) (5.17 g, 4.48 mmol). The mixture was heated to 60° C. for 4 hours and then the palladium catalyst was filtered off. To the filtrate were added water (100 mL) and a saturated ammonium chloride solution (150 mL). After extracting with ethyl acetate (3×100 mL), the organic portions were combined, washed with brine (150 mL), dried (MgSO4) and concentrated. The crude material was purified by column utilizing 5% EtOAc/hexanes as the eluent to produce 2.12 g of 2-bromo-4-(4-fluoro-benzyl)-1-methoxy-benzene as a colorless oil in 40% yield.

Provenance & Evidence