Water → 4-broMo-1-Methyl-1H-iMidazole-2-carbaldehyde

HRID 509611Notes

Reaction equation

HRID 509611 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH:7]=[O:8].[Br:9]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:9][C:5]1[N:4]=[C:3]([CH:7]=[O:8])[N:2]([CH3:1])[CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 1395751-Methyl-2-imidazolecarboxaldehyde

Product 1

HCID 127422794-broMo-1-Methyl-1H-iMidazole-2-carbaldehydeYield 43.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-methyl-1H-imidazole-2-carbaldehyde (10 g, 90 mmol) in deoxygenated DMF (300 mL) was treated with N-bromosuccinimide (17.8 g, 100 mmol) and the resulting solution stirred at RT for 6 days. Water (750 mL) was added and the resulting mixture was extracted with EtOAc (4×200 mL) the combined extracts were dried over Na2SO4, filtered and the volatiles removed in vacuo. The residue was purified by column chromatography on silica gel (n-heptane/EtOAc=4/1) to yield the title compound (7.33 g, 40%) as a white solid. LC-MS: m/z=191.2 (MH+), tR=0.48 minutes, method A. 1H NMR (600 MHz, DMSO-d6): δ 9.62 (s, 1H), 7.80 (s, 1H), 3.92 (s, 3H).

Workup

  1. extractionthe resulting mixture was extracted with EtOAc (4×200 mL) the combined extracts
  2. dry with materialwere dried over Na2SO4
  3. filtrationfiltered
  4. customthe volatiles removed in vacuo
  5. customThe residue was purified by column chromatography on silica gel (n-heptane/EtOAc=4/1)

Sources & evidence

ORD record
ord-bc41593904d5483e9166ca0a6c5cd9e7
Source dataset
uspto-grants-2015_08
Patent number
US09096589B2

Reaction notes

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