Allyl bromide → 1-allyl-2-bromo-1H-benzo[d]imidazole

HRID 1051729노트

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HRID 1051729 반응식
[Br:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.[CH2:11](Br)[CH:12]=[CH2:13].O1CCOCC1.[OH-].[Na+]>C(OCC)(=O)C>[CH2:13]([N:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[Br:1])[CH:12]=[CH2:11]

참가 물질

6

반응물 4

HCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 27762812-Bromobenzimidazole

생성물 1

HCID 1180762101-allyl-2-bromo-1H-benzo[d]imidazole수율 52%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

A mixture of 2-bromo-1H-benzo[d]imidazole (0.400 g, 2.04 mmol), allyl bromide (0.35 mL, 4.08 mmol), 1,4-dioxane (15 mL), and 2 M aqueous sodium hydroxide solution (15 mL, 3.00 mmol) stirred for 2 h at 100° C. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (50 mL). The organic phase was separated and washed with brine (30 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via preparative thin layer chromatography (eluting with 20% ethyl acetate/petroleum ether) to afford 1-allyl-2-bromo-1H-benzo[d]imidazole (0.251 g, 52%) as a yellow oil. MS (ESI, pos. ion) m/z 237, 239 [M+H]+.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe organic phase was separated
  3. washwashed with brine (30 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified via preparative thin layer chromatography (eluting with 20% ethyl acetate/petroleum ether)

출처 및 근거

ORD 기록
ord-7205731dc75748158df4228c83848a72
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388161B2

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