1-(Bromomethyl)-2-phenylbenzene → Biphenyl imidazole

HRID 22045

반응식

HRID 22045 반응식
C([C:5]1[NH:6][CH:7]=[CH:8][N:9]=1)CCC.CC(C)([O-])C.[K+].BrC[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C>[NH:6]1[CH:7]=[CH:8][N:9]=[CH:5]1.[C:19]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:18]=1

참가 물질

5

반응물 3

HCID 2633651-(Bromomethyl)-2-phenylbenzeneHCID 118153512-butyl-1H-imidazoleHCID 23665647Potassium tert-butoxide

생성물 1

HCID 21941119Biphenyl imidazole수율 98.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4.07 g (32.8 mmol) of 2-butylimidazole (obtained from step 1) in 110 mL of DMF was added 44.3 mL (44.3 mmol) of potassium tert-butoxide (1M in THF), and the resulting solution was stirred at room temperature for 15 min. To the dark brown mixture was added 20.1 g (36.1 mmol) of the bromomethyl biphenyl. The reaction mixture was stirred at room temperature for 16 h, and concentrated in vacuo. The residue was dissolved in chloroform and washed with water. The aqueous layer was extracted with fresh chloroform, and the combined extracts were dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography to give 7.2 g (37%) of the biphenyl imidazole intermediate as a yellow oil which solidified as a glass: 1H NMR (CDCl3) δ 0.90 (t, J=7.31 Hz, 3H), 1.35 (septet, J=7.5 Hz, 2H), 1.71 (quintet, J=7.74 Hz, 2H), 2.61 (t, J=7.58 Hz, 2H), 4.93 (s, 2H), 6.65 (d, J=1.35 Hz, 1H), 6.79 (d, J=8.31 Hz, 2H), 6.92 (d, J=7.3 Hz, 6H), 6.97 (d, J=1.32 Hz, 1H), 7.11 (d, J=8.2 Hz, 2H), 7.2-7.4 (m, 10H), 7.4-7.55 (m, 2H), 7.95 (dd, J=6.85, 2.08 Hz, 1H); MS(FAB) m/e (relative intensity) 607 (100, M+Li), 601 (90, M+H).

후처리

  1. stirringThe reaction mixture was stirred at room temperature for 16 h
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in chloroform
  4. washwashed with water
  5. extractionThe aqueous layer was extracted with fresh chloroform
  6. dry with materialthe combined extracts were dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography

출처 및 근거

ORD 기록
ord-154a35f741314c1f889b1e3408a6515f
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05426105

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