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

HRID 2188015
ノート
印刷プレビュー

反応式

HRID 2188015 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 749781,1'-Azobis(cyclohexanecarbonitrile)触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-40cd6be5a9694487a57f2b1ffa13d5d7
出典データセット
uspto-grants-2002_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06410556B1

反応ノート

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