Triethylamine → 4-[2-(Tert-butyldimethylsilanyloxy)ethoxy]bromobenzene

HRID 873640ノート

反応式

HRID 873640 の反応式
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8][OH:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>ClCCl.CN(C)C1C=CN=CC=1>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8][O:9][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 991682-(p-Bromophenoxy)ethanol

生成物 1

HCID 150978074-[2-(Tert-butyldimethylsilanyloxy)ethoxy]bromobenzene収率 98.4%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

2-(4-Bromo-phenoxy)-ethanol (5 g, 23 mmol) is dissolved in dichloromethane (40 mL). Triethylamine (2.8 g, 28 mmol) and 4-dimethylaminopyridine (140 mg, 1.15 mmol) were then added followed by tert-butyldimethylsilyl chloride (3.65 g, 24.3 mmol) as a solution in dichloromethane (10 mL). The reaction is allowed to stir at ambient temperature for 18 hours. The reaction mixture is washed with 10% aqueous citric acid, the organic layer is separated and concentrated in vacuo to afford 7.5 g (98% yield) of the title compound. 1H NMR (CDCl3) 0.05 (s, 6H), 0.85 (s, 9H), 3.85-3.94 (m, 4H), 6.72 (d, 2H, J=6.90 Hz), 7.28 (d, 2H, J=6.90 Hz).

後処理

  1. washThe reaction mixture is washed with 10% aqueous citric acid
  2. customthe organic layer is separated
  3. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-ab3eebfce66d4e11b2af79c9182f61f0
出典データセット
uspto-grants-2015_03
特許番号
US08975439B2

反応ノート

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