Imidazole → 2-[2-[[Dimethyl(1,1,2-trimethylpropyl)silyl]oxy]ethyl]benzene bromide

HRID 465868

반응식

HRID 465868 반응식
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5][OH:6].N1C=CN=C1.[CH3:16][Si:17](Cl)([CH3:24])[C:18]([CH:21]([CH3:23])[CH3:22])([CH3:20])[CH3:19]>C(Cl)Cl.O.CCOCC>[Br-:1].[CH3:16][Si:17]([CH3:24])([C:18]([CH3:20])([CH3:19])[CH:21]([CH3:23])[CH3:22])[O:6][CH2:5][CH2:4][C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:2]=1

참가 물질

7

반응물 3

HCID 795ImidazoleHCID 144239Dimethylthexylsilyl chlorideHCID 27340892-(2-Bromophenyl)ethan-1-ol

생성물 1

HCID 198753762-[2-[[Dimethyl(1,1,2-trimethylpropyl)silyl]oxy]ethyl]benzene bromide

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

2-Bromophenethyl alcohol (43.80 g, 217.9 mmol) was dissolved in anhydrous CH2Cl2 (200 mL) and imidazole (16.32 g, 239.6 mmol) was added and stirred under argon 0° C. Dimethylthexylsilyl chloride (42.83 g, 239.6 mmol) was added dropwise and the reaction mixture was stirred for three days at room temperature. It was diluted with H2O (50 mL) and ether (100 mL) and partitioned. The aqueous layer was extracted with ether (2×100 mL). The combined organic layers were washed with 5% aqueous HCl (1 time), H2O (1 time), aqueous NaHCO3 (1 time), H2O (1 time), and brine, then dried (MgSO4) and concentrated in vacuo to obtain a yellow oil. The crude product was Kugelrohr distilled (55°-80° ) under oil pump vacuum to give the purified title compound.

후처리

  1. stirringthe reaction mixture was stirred for three days at room temperature
  2. custompartitioned
  3. extractionThe aqueous layer was extracted with ether (2×100 mL)
  4. washThe combined organic layers were washed with 5% aqueous HCl (1 time), H2O (1 time), aqueous NaHCO3 (1 time), H2O (1 time), and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto obtain a yellow oil
  8. distillationdistilled (55°-80° ) under oil pump vacuum
  9. customto give the
  10. custompurified title compound

출처 및 근거

ORD 기록
ord-a0c538e554cc4726895b1e987c7f877d
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05153327

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