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

HRID 22045

Reaction equation

HRID 22045 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 21941119Biphenyl imidazoleYield 98.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-154a35f741314c1f889b1e3408a6515f
Source dataset
uspto-grants-1995_06
Patent number
US05426105

Linked notes

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