Ethyl chloroformate → Ethyl 5-bromo-1-methyl-1H-imidazole-2-carboxylate

HRID 2109200Notes

Reaction equation

HRID 2109200 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[Br:7][C:8]1[N:12]([CH3:13])[CH:11]=[N:10][CH:9]=1>CC#N>[CH2:5]([O:4][C:2]([C:11]1[N:12]([CH3:13])[C:8]([Br:7])=[CH:9][N:10]=1)=[O:3])[CH3:6]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 15152585-Bromo-1-methyl-1H-imidazole

Product 1

HCID 58861475Ethyl 5-bromo-1-methyl-1H-imidazole-2-carboxylateYield 55.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Ethyl chloroformate (1.19 mL, 12.4 mmol) in MeCN (5 mL) was added dropwise to a 1.00 g (6.21 mmol) of 5-bromo-1-methyl-1H-imidazole (Aldrich) in 30 mL of MeCN under N2. The mixture was stirred and allowed to warm to rt overnight. The mixture was concentrated and the residue was treated with 2M NaOH (100 mL) and extratcted with CH2Cl2 (3×100 mL). The combined extracts were washed with brine, dried with MgSO4, filtered, concentrated, and chromatographed (0-50% EtOAc in hexanes) to give the 5-bromo-1-methyl-1H-imidazole-2-carboxylic acid ethyl ester as a yellow oil (800 mg).

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue was treated with 2M NaOH (100 mL)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed (0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-9330a61fd0ae4756b317b49b52fd18f1
Source dataset
uspto-grants-2009_04
Patent number
US07514458B2

Reaction notes

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