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

HRID 81549
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HRID 81549 반응식
[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]
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5

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HCID 11561Benzene, 1-bromo-3-iodo-HCID 5706451Ethyl 2-((tert-butoxycarbonyl)imino)-3,3,3-trifluoropropanoateHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 666657032-(3-Bromo-phenyl)-2-tert-butoxycarbonylamino-3,3,3-trifluoro-propionic acid ethyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-0fe51288042c4bebbc75f7123b607156
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08846658B2

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