Iodine → Tert-butyl 2-iodo-6-methoxyphenylcarbamate

Participants

Reaction Conditions

Reaction Steps

To tert-butyl 2-methoxyphenylcarbamate (24.1 g, 108 mmol) in dry Et2O (100 mL) at −20° C. was added dropwise tert-butyllithium (140 ml, 237 mmol). The clear solution turned cloudy at the end of the addition. The reaction was stirred for 3 hours at −20° C., then cooled to −100° C. with a liquid N2/Et2O bath. Iodine (27.4 g, 108 mmol) in Et2O (250 mL) was added to the solution. Following addition of I2, the reaction was slowly warmed to ambient temperature over night. Na2S2O3 (saturated, 200 mL) was then added to the reaction mix and phases were separated. The aqueous was extracted with Et2O, and the combined organic layers were dried (MgSO4), filtered and concentrated. DCM (50 mL) was added, followed by hexanes (200 mL). The solution was concentrated to remove DCM. The product crashed out, and was collected by filtration and washed with hexanes (100 mL) to give the crude product (58%).

Provenance & Evidence