Benzene, 1-bromo-3-iodo- → 2-(3-Bromo-phenyl)-2-tert-butoxycarbonylamino-3,3,3-trifluoro-propionic acid ethyl ester

Temperature

0 °C

A solution of 5.66 g (20 mmol) 1-bromo-3-iodo-benzene in 25 ml THF was stirred at −20° C. A 1.82 M solution of isopropylmagnesium chloride (12.1 ml, 22.0 mmol) in THF was added and the mixture was stirred 1 h at 0° C. The mixture was cooled to −78° C. and a solution of 5.38 g (20 mmol) 2-[(E)-tert-butoxycarbonylimino]-3,3,3-trifluoro-propionic acid ethyl ester in 50 ml of THF was added over a period of 2 h. After 20 min the mixture was quenched with 5% aqueous NH4Cl. The mixture was extracted with TBME. The organic phase was dried with Na2SO4, filtered and evaporated. Purification via chromatography on silica gel (c-hexane/0-14% EtOAc) gave the desired product as a colorless resin.

1. temperatureThe mixture was cooled to −78° C.
2. customAfter 20 min the mixture was quenched with 5% aqueous NH4Cl
3. extractionThe mixture was extracted with TBME
4. dry with materialThe organic phase was dried with Na2SO4
5. filtrationfiltered
6. customevaporated
7. customPurification via chromatography on silica gel (c-hexane/0-14% EtOAc)

ORD record

ord-0fe51288042c4bebbc75f7123b607156

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846658B2