Imidazole → 4-Bromophenyl-tert-butyldimethylsilyl ether

HRID 1489400

反応式

HRID 1489400 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5](O)=[CH:4][CH:3]=1.N1[CH:13]=[CH:12]N=C1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].[OH2:22]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:15][Si:14]([O:22][Si:14]([CH2:16][C:13]2[CH:12]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)([CH3:15])[C:17]([CH3:20])([CH3:19])[CH3:18])([C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:16])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 795ImidazoleHCID 962WaterHCID 78084-BromophenolHCID 28928tert-Butyldimethylsilyl chloride

生成物 1

HCID 688013174-Bromophenyl-tert-butyldimethylsilyl ether

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

4-Bromophenol (5.76 g, 30 mmol), imidazole (4.08 g, 60 mmol) and tert-butyldimethylsilyl chloride (5.02 g, 33 mmol) were stirred in anhydrous DMF (100 mL) at 25° C. for 18 h. The reaction mixture was then poured into water (100 mL) and extracted with ethyl acetate (2×75 mL). The combined extracts were washed with water (2×75 mL), brine (75 mL) and dried (MgSO4) before concentration in vacuo. The crude product was purified using "flash" silica gel column chromatography with ethyl acetate:hexane (1:4) as eluant to afford the title compound as an oil, 7.9 g, 92%. 1H NMR (CDCl3, 300 MHz): δ 7.33 (app. dt, J=9, 3, 1 Hz, 2 H), 6.73 (app. dt, J=9, 3, 1 Hz, 2 H) 0.98 (s, 9 H),0.21 (s, 6 H).

後処理

  1. extractionextracted with ethyl acetate (2×75 mL)
  2. washThe combined extracts were washed with water (2×75 mL), brine (75 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationbefore concentration in vacuo
  5. customThe crude product was purified

出典と根拠

ORDレコード
ord-947c64e524e744f09e00b12249db8bf8
出典データセット
uspto-grants-1997_10
特許番号
US05677459

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