Cesium carbonate → 4-bromo-1-(2-methoxy-4-nitro-phenyl)-1H-imidazole

HRID 604923Notes

Reaction equation

HRID 604923 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH3:12].[Br:13][C:14]1[N:15]=[CH:16][NH:17][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[Br:13][C:14]1[N:15]=[CH:16][N:17]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=2[O:11][CH3:12])[CH:18]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 705192-Chloro-5-nitroanisoleHCID 178418934HCID 178418934, compound

Product 1

HCID 668864944-bromo-1-(2-methoxy-4-nitro-phenyl)-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2.0 g (10.7 mmol) 2-chloro-5-nitroanisole, 1.65 g (11.2 mmol) 4-bromoimidazole and 5.21 g (16.0 mmol) cesium carbonate in 50 ml acetonitrile was refluxed overnight. The reaction mixture was concentrated, diluted with water and extracted with ethyl acetate. The organic phase was dried, evaporated and the residue purified on silica gel with ethyl acetate/heptane 3/7. After trituration with diethyl ether 707 mg (22%) of 4-bromo-1-(2-methoxy-4-nitro-phenyl)-1H-imidazole was isolated as a slightly brownish solid. MS ISP (m/e): 298.1/300.0 (100/87) (M+H)+. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.96 (d, 2H), 7.77 (s, 1H), 7.44 (d, 1H), 7.26 (s, 1H), 4.02 (s, 3H).

Workup

  1. temperaturewas refluxed overnight
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. customThe organic phase was dried
  6. customevaporated
  7. customthe residue purified on silica gel with ethyl acetate/heptane 3/7

Sources & evidence

ORD record
ord-5766042e60f14df19697605aaccba6ad
Source dataset
uspto-grants-2011_03
Patent number
US07910740B2

Reaction notes

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