Acetonitrile → 4-bromo-5-(4-chlorophenyl)-1-methyl-1H-imidazole

HRID 1506657Notes

Reaction equation

HRID 1506657 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH3:13])[CH:10]=CN=2)=[CH:4][CH:3]=1.C1C(=O)N([Br:21])C(=O)C1.[C:22](#[N:24])C>>[Br:21][C:22]1[N:24]=[CH:10][N:9]([CH3:13])[C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 67184N-bromobutanimideHCID 10856331(4-Chlorophenyl)-1-methyl-1H-imidazole

Product 1

HCID 251721464-bromo-5-(4-chlorophenyl)-1-methyl-1H-imidazole

Conditions

Temperature
0 °C

Procedure

(4-Chlorophenyl)-1-methyl-1H-imidazole (3 g, 15.5 mmol) was dissolved in ACN (150 mL) and cooled to 0° C. NBS (2.76 g, 15.5 mmol) was added in 3 portions over 5 min. The reaction was stirred at 0° C. for 20 min then let warm to ambient temperature. Solvents were removed in vacuo and the residue partitioned between EtOAc and 20% aqueous KH2PO4. The organics were separated, washed with saturated aqueous NaHCO3, and dried with saturated aqueous NaCl. Solvents were removed in vacuo and the residue purified by column chromatography on silica to provide the desired product. MS (m/z) 273.1 [M+H]+.

Workup

  1. temperaturethen let warm to ambient temperature
  2. customSolvents were removed in vacuo
  3. customthe residue partitioned between EtOAc and 20% aqueous KH2PO4
  4. customThe organics were separated
  5. washwashed with saturated aqueous NaHCO3
  6. dry with materialdried with saturated aqueous NaCl
  7. customSolvents were removed in vacuo
  8. customthe residue purified by column chromatography on silica

Sources & evidence

ORD record
ord-41c6eccd80504082ae7e6b03564163d4
Source dataset
uspto-grants-2015_12
Patent number
US09220710B2

Reaction notes

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