Diisopropylamine → Methyl 3-bromo-5-(prop-1-en-2-yl)benzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-bromo-5-iodobenzoate (2.50 g, 7.33 mmol) in acetonitrile (22.0 mL) and water (7.33 mL) was 2-isopropenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.378 mL, 7.33 mmol), palladium(II) acetate (41.0 mg, 0.183 mmol), 3,3′3″-phosphinidynetris(benzenesulfonic acid)trisodium salt (313 mg, 0.550 mmol) and diisopropylamine (2.61 mL, 18.33 mmol) and the mixture was heated to 80° C. After 2.5 h, the reaction was allowed to cool to ambient temperature and saturated aqueous sodium bicarbonate was added. The mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→80% hexanes/ethyl acetate) gave the title compound (1.71 g).

Provenance & Evidence