Imidazole → ((3-Bromo-5-nitrobenzyl)oxy)(tert-butyl)dimethylsilane

HRID 410455

반응식

HRID 410455 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)[CH2:5][OH:6].[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].N1C=CN=C1>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)[CH2:5][O:6][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 14866972(3-Bromo-5-nitrophenyl)methanol

생성물 1

HCID 67431768((3-Bromo-5-nitrobenzyl)oxy)(tert-butyl)dimethylsilane수율 93.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 3-bromo-5-nitrobenzyl alcohol (5 g, 21.5 mmol), in N,N-dimethylformamide (5 mL) was treated with tert-butyldimethylsilyl chloride (4.9 g, 32.3 mmol) and imidazole (2.5 g, 36.6 mmol) and stirred at room temperature for 14 h. The reaction was quenched with water and extracted with ethyl acetate (2×). The organic layer was dried over sodium sulfate, filtered, and concentrated. Purification by flash chromatography on silica (0-75% ethyl acetate in hexanes) afforded [(3-bromo-5-nitrobenzyl)oxy](tert-butyl)dimethylsilane (7.32 g, 20.1 mmol, 93% yield) as a yellow oil.

후처리

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate (2×)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography on silica (0-75% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-02d77ed9143d4fda8cea5d789f2aa38f
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759366B2

연결된 노트

불러오는 중…