Benzene → Methyl 3-bromo-5-methanesulfonylbenzoate

Participants

Reaction Steps

To a sealable tube equipped with a stir bar were added (CuOTf)2.PhH (164 mg, 0.29 mmol), sodium methanesulfinate (847.8 mg, 7.06 mmol) and 3-bromo-5-iodobenzoate (2.0 g, 5.88 mmol). The tube was then covered with a rubber septa and a nitrogen atmosphere was established. N,N′-dimethylethylenediamine (54.6 mg, 0.07 mL, 0.588 mmol) and anhydrous DMSO (5.88 mL) were added via syringe and the septa was replaced by a Teflon-coated screw cap and the reaction vessel was placed in a 110° C. oil bath. After stirred for 20 h, the reaction mixture was allowed to cool to room temperature, diluted with ethyl acetate (60 mL) and filtered through a pad of silica gel. The filtrate was washed with H2O (100 mL) twice, brine (100 mL), dried over sodium sulfate, filtered and concentrated under vacuum. The crude mixture was purified by reverse phase prep HPLC to give the title compound (760 mg): 1H NMR (CD3OD, 500 MHz) δ ppm 3.21 (3H, s), 3.99 (3H, s), 8.36 (1H, m), 8.46 (1H, m), 8.50 (1H, m). HPLC retention time: 1.578 min (method A). MS (ESI) (M+H)+ 292.00.

Provenance & Evidence