2-Methyl-2-butene → 4-bromo-2-methyl-1H-imidazole-5-carboxylic acid

HRID 1874853Notes

Reaction equation

HRID 1874853 reaction equation
Cl([O-])=O.[Na+].[OH2:5].P([O-])(O)(O)=O.[Na+].[Br:12][C:13]1[N:14]=[C:15]([CH3:20])[NH:16][C:17]=1[CH:18]=[O:19].CC(=CC)C>O.C1COCC1.C(O)(C)(C)C>[Br:12][C:13]1[N:14]=[C:15]([CH3:20])[NH:16][C:17]=1[C:18]([OH:5])=[O:19]

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 23668197Sodium ChloriteHCID 178432447HCID 178432447, compound

Product 1

HCID 1784324484-bromo-2-methyl-1H-imidazole-5-carboxylic acidYield 87%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of sodium chlorite (1.6 g, 17.8 mmol) and sodium dihydrogen phosphate monohydrate (1.5 g, 10.6 mmol) in water (3.9 mL) was added to a stirred solution of 4-bromo-2-methyl-1H-imidazole-5-carbaldehyde (0.334 g, 1.8 mmol), 2-methyl-2-butene (11 mL of a 2M solution in THF, 22.0 mmol), and tert-butanol (1.3 mL) in THF (5.5 mL). The reaction mixture was stirred at RT for 6 h. The aqueous phase was separated and extracted with EtOAc (4×10 mL). The combined extracts were dried (Na2SO4), filtered, concentrated and the residue was triturated with diethyl ether to provide the title compound (0.316 g, 87%) as white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.91 (br. s., 1H), 2.27 (s, 3H). ES-LCMS: m/z 205.2, 207.3 (M+1).

Workup

  1. customThe aqueous phase was separated
  2. extractionextracted with EtOAc (4×10 mL)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-c6b2d78f132b4326998a52a4ea89b0d6
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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