Iodine → HCID 59200408, compound

Participants

Reaction Steps

3-Bromotoluene (0.8 mL, 6.6 mmol) was added to Mg turnings (0.312 g, 13 mmol) in diethyl ether (5 mL) and an iodine crystal was also added. The reaction was stirred for 30 minutes. The solution was then transferred to another flask (via a pipet) to separate from the excess Mg. A solution of carbobenzyloxyglycine methyl ester (0.294 g, 1.32 mmol) in diethyl ether (3 mL) was then added to the solution of the Grignard reagent and the reaction was stirred for 1 hour. The reaction was then quenched with sat. aq ammonium chloride and the aqueous phase was extracted with ethyl acetate (3×). The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified on Biotage chromatography (10% to 10% ethyl acetate/hexane) to give the title material (0.309 g, 62%) as an oil. 1H NMR (400 MHz, DMSO-d6) δ: 2.26 (6H, s), 3.82 (2H, d, J=5.81 Hz), 4.99 (2H, s), 5.76 (1H, s), 6.79 (1H, t, J=5.56 Hz), 7.01 (2H, d, J=7.07 Hz), 7.09-7.40 (11H, m). LC/MS (M−H)−: 374. HPLC ret. time (Condition B): 2.133 min.

Provenance & Evidence