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N-bromobutanimide → 6-Bromomethyl-2-(tert-butyl-dimethyl-silanyloxy)-benzoic acid ethyl ester

HRID 2188015
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HRID 2188015 반응식
[CH2:1]([O:3][C:4](=[O:20])[C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]=1[O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH3:2].[Br:21]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl.N(C1(C#N)CCCCC1)=NC1(C#N)CCCCC1>[CH2:1]([O:3][C:4](=[O:20])[C:5]1[C:10]([CH2:11][Br:21])=[CH:9][CH:8]=[CH:7][C:6]=1[O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH3:2]
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참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 69585527Ethyl 2-((tert-butyldimethylsilyl)oxy)-6-methylbenzoate

생성물 1

HCID 695855186-Bromomethyl-2-(tert-butyl-dimethyl-silanyloxy)-benzoic acid ethyl ester수율 83.1%

시약·촉매·용매 2

HCID 749781,1'-Azobis(cyclohexanecarbonitrile)촉매HCID 5943Carbon Tetrachloride용매

실험 절차

2-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-benzoic acid ethyl ester (7.6 g, 25.8 mmol), N-bromosuccinimide (4.82 g, 27.1 mmol) and azobis(cyclohexanecarbonitrile) (0.32 g, 1.3 mmol) were dissolved in tetrachlormethane (130 ml). The solution was stirred at room temperature for 60 hours. The solvent was evaporated in vacuo and the residue was chromatographed on silica gel column using a gradient of 1-2% ethyl acetate/hexane as eluent, which afforded 8.0 g (83%) of 6-bromomethyl-2-(tert-butyl-dimethyl-silanyloxy)-benzoic acid ethyl ester as an oil.

후처리

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was chromatographed on silica gel column

출처 및 근거

ORD 기록
ord-40cd6be5a9694487a57f2b1ffa13d5d7
출처 데이터셋
uspto-grants-2002_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06410556B1

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