Benzyl Bromide → 1-benzylimidazole-4-carbaldehyde

HRID 1509857Notes

Reaction equation

HRID 1509857 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1C=O.[C:8](=[O:11])([O-])[O-].[Na+].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C>[CH2:14]([N:3]1[CH:4]=[C:5]([CH:8]=[O:11])[N:1]=[CH:2]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 249551H-imidazole-2-carbaldehyde

Product 1

HCID 110953111-benzylimidazole-4-carbaldehydeYield 58.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

To a solution of imidazolecarboxaldehyde (1.0 g, 10.4 mmol) in DMF (10 mL) was added sodium carbonate (2.2 g, 20.8 mmol). The mixture was then treated with a solution of benzyl bromide (1.77 g, 10.4 mmol) in DMF (5 mL) dropwise and stirred for 1 h at 100° C. The reaction mixture was partitioned between EtOAc and water, and the aqueous layer was extracted with EtOAc. The organic layers were combined, dried with MgSO4, filtered, and concentrated to yield a dark brown oil (1.14 g). (m/z): [M+H]+calcd for C11H10N2O 187.21; found, 187.3. 1H NMR (d6-DMSO, 400 MHz) δ (ppm): 9.67 (s, 1H), 8.22, 8.08, 7.96, 7.90 (4 sets of singlets, total 2H), 7.30-7.24 (m, 5H), 5.49 (s, 1H), 5.25 (s, 1H).

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. extractionthe aqueous layer was extracted with EtOAc
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fa614144e6ae40728899606b97906da2
Source dataset
uspto-grants-2012_07
Patent number
US08211894B2

Reaction notes

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