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

HRID 22045

Reaktionsgleichung

Reaktionsgleichung von HRID 22045
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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 21941119Biphenyl imidazoleAusbeute 98,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-154a35f741314c1f889b1e3408a6515f
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05426105

Verknüpfte Notizen

Wird geladen…