Benzyl Bromide → 1-benzyl-1H-imidazole-2-carbaldehyde

HRID 1968155Notes

Reaction equation

HRID 1968155 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7].C(=O)([O-])[O-].[K+].[K+].Br[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(#N)C>[CH2:15]([N:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 249551H-imidazole-2-carbaldehyde

Product 1

HCID 1390821-benzyl-1H-imidazole-2-carbaldehydeYield 96.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 1H-imidazole-2-carbaldehyde (240 mg, 2.4 mmol) and potassium carbonate (662 mg, 4.8 mmol) in acetonitrile (5 mL) at 0° C. was added dropwise (bromomethyl)benzene (493 mg, 2.88 mmol). The mixture was stirred at 40° C. for 4 hr. Then the mixture was filtrated, evaporated to remove the acetonitrile from the filtrate, added EtOAc to extract the residues, and washed the extract with brine and water. The organic layer was dried with anhydrous Na2SO4, concentrated, and chromatographed on a silica gel column (EtOAc:hexane=1:9) to obtain the title compound (430 mg, yield 95%). LC-MS (ESI) m/z: 187 (M+1)+.

Workup

  1. filtrationThen the mixture was filtrated
  2. customevaporated
  3. customto remove the acetonitrile from the filtrate
  4. additionadded EtOAc
  5. extractionto extract the residues
  6. washwashed the
  7. extractionextract with brine and water
  8. dry with materialThe organic layer was dried with anhydrous Na2SO4
  9. concentrationconcentrated
  10. customchromatographed on a silica gel column (EtOAc:hexane=1:9)

Sources & evidence

ORD record
ord-fe0b70b956df4ae6ac3c8b39f49b4f6e
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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