Imidazole → 4-Bromo-2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-1-methoxybenzene

HRID 1375977ノート

反応式

HRID 1375977 の反応式
N1C=CN=C1.[C:6]([Si:10]([CH3:13])([CH3:12])Cl)([CH3:9])([CH3:8])[CH3:7].[Br:14][C:15]1[CH:16]=[CH:17][C:18]([O:23][CH3:24])=[C:19]([CH:22]=1)[CH2:20][OH:21].O>CN(C=O)C>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([O:23][CH3:24])=[C:19]([CH:22]=1)[CH2:20][O:21][Si:10]([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:13])[CH3:12]

参加物

6

反応物 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 6122985-Bromo-2-methoxybenzyl alcohol

生成物 1

HCID 120384334-Bromo-2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-1-methoxybenzene収率 99.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Imidazole (3.45 g) and t-butyldimethylchlorosilane (17.6 g) were added to a solution of 5-bromo-2-methoxybenzyl alcohol (10.0 g) in DMF (100 ml) under cooling with ice and the mixture was stirred for two hours. The reaction mixture was added to ice-cooled water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated. The residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain [(5-bromo-2-methoxybenzyl)oxy](t-butyl)dimethylsilane (15.2 g).

後処理

  1. temperatureunder cooling with ice
  2. additionThe reaction mixture was added to ice-
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by silica gel column chromatography (n-hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-1695856f7ede479dbd469d50171e3729
出典データセット
uspto-grants-2007_01
特許番号
US07169761B2

反応ノート

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