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

HRID 81549

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](I)[CH:3]=1.C([Mg]Cl)(C)C.[CH2:14]([O:16][C:17](=[O:31])/[C:18](=[N:23]\[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])/[C:19]([F:22])([F:21])[F:20])[CH3:15]>C1COCC1>[CH2:14]([O:16][C:17](=[O:31])[C:18]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:19]([F:22])([F:21])[F:20])[CH3:15]

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-0fe51288042c4bebbc75f7123b607156
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846658B2

Linked notes

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