Iodine → tert-Butyl 2-iodo-3-methoxyphenylcarbamate

To the solution of tert-butyl (3-methoxyphenyl)-carbamate (5 g, 22.4 mmol, 1 eq) in dry diethyl ether (50 mL) was added pentane solution of t-BuLi (35 mL, 49.3 mmol, 2.2 eq) at −20° C., and the mixture was stirred at 3 hours. To this mixed solution was added the solution of iodine (6.83 g, 26.9 mmol, 1.2 eq) in diethylether (60 mL) at −78° C., and after heating the whole solution to room temperature, the solution was stirred for 20 hours. After adding saturated aqueous solution of Na2S2O3 (100 mL), the mixture was extracted three times with diethyl ether (100 mL). The extract was washed with aqueous solution of sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting concentrate was applied to silica gel (eluate: hexane-AcOEt=90-10) to give white solid of the title compound (5.755 g, yield 74%).

1. stirringthe solution was stirred for 20 hours
2. extractionthe mixture was extracted three times with diethyl ether (100 mL)
3. washThe extract was washed with aqueous solution of sodium chloride
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. concentrationThe resulting concentrate

ORD record

ord-ffb6486576f745de8f9688429be8ea3e

Source dataset

uspto-grants-2007_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07307098B2