Sodium Methoxide → methyl 4-bromo-1-methyl-1H-imidazole-2-carboxylate
Reaction equation
[Br:1][C:2]1[N:3]=[C:4]([C:8](=[O:13])C(Cl)(Cl)Cl)[N:5]([CH3:7])[CH:6]=1.[CH3:14][O-:15].[Na+]>CO>[CH3:14][O:15][C:8]([C:4]1[N:5]([CH3:7])[CH:6]=[C:2]([Br:1])[N:3]=1)=[O:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To the solution of 1.18 g of 1-(-4-bromo-1-methyl-1H-imidazol-2-yl)-2,2,2-trichloroethanone in 10 mL of methanol was added 42 mg of sodium methoxide and the resulting mixture was stirred at 25° C. for 20 min. TLC showed completion of the reaction. The solution was evaporated, redissolved in 30 mL of DCM, washed with water (15 mL×2) and brine (15 mL). The solution was dried over anhydrous sodium sulfate and filtered. The residue was purified by silica gel column (DCM/MeOH=60/1) to give 4-bromo-1-methyl-1H-imidazole-2-carboxylic acid methyl ester (0.575 g, yield 68%). 1H NMR (300 MHz, CDCl3) δ 7.02 (s, 1H), 4.00 (s, 3H). 3.93 (s, 3H). LC-MS calcd for C6H7BrN2O2 (m/e) 217.97, obsd 219 and 221 [M+1]+
Workup
- customcompletion of the reaction
- customThe solution was evaporated
- dissolutionredissolved in 30 mL of DCM
- washwashed with water (15 mL×2) and brine (15 mL)
- dry with materialThe solution was dried over anhydrous sodium sulfate
- filtrationfiltered
- customThe residue was purified by silica gel column (DCM/MeOH=60/1)
Sources & evidence
- ORD record
- ord-94ba507a7eb14213a5a2411c3308ce10
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08729078B2
Reaction notes
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