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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
ノート
印刷プレビュー

反応式

HRID 81549 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-0fe51288042c4bebbc75f7123b607156
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08846658B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート