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

Temperature

-20 °C

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%).

1. additionThe clear solution turned cloudy at the end of the addition
2. temperaturecooled to −100° C. with a liquid N2/Et2O bath
3. temperaturethe reaction was slowly warmed to ambient temperature over night
4. additionmix
5. customphases were separated
6. extractionThe aqueous was extracted with Et2O
7. dry with materialthe combined organic layers were dried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated
10. additionDCM (50 mL) was added
11. concentrationThe solution was concentrated
12. customto remove DCM
13. filtrationwas collected by filtration
14. washwashed with hexanes (100 mL)

ORD record

ord-8289641f9dde4125be356749b745009f

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08138181B2