Carbon Dioxide → HCID 58506078, compound

HRID 1627231Notes

Reaction equation

HRID 1627231 reaction equation
Br[C:2]1[N:3]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[C:4]([Br:8])=[C:5]([Br:7])[N:6]=1.C1([Li])C=CC=CC=1.[C:24](=[O:26])=[O:25].Cl>O1CCCC1.O>[Br:7][C:5]1[N:6]=[C:2]([C:24]([OH:26])=[O:25])[N:3]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[C:4]=1[Br:8]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 109062032,4,5-tribromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-ImidazoleHCID 178506676HCID 178506676, compound

Product 1

HCID 58506078HCID 58506078, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 2,4,5-tribromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole (5.0 g, 11.5 mmol) in tetrahydrofuran (200 ml) at −78° C. is added phenyl lithium (7.0 ml, 12.6 mmol, 1.8 M in THF). After 30 minutes stirring at −78° C. CO2-pellets (˜3.0 g) are added. The mixture is allowed to warm to room temperature, water is added, and the pH is carefully adjusted with 6N HCl (aqueous) to pH=5. The mixture is extracted with ethyl acetate (2×50 ml) and the combined organic layer is washed with brine, dried over MgSO4, filtered and evaporated in vacuo. The crude 4,5-dibromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid is obtained as a yellow oil, and used without further purification 4.2 g, 91%, LC/MS ESI m/z (M−H)−398.8.

Workup

  1. temperatureto warm to room temperature
  2. extractionThe mixture is extracted with ethyl acetate (2×50 ml)
  3. washthe combined organic layer is washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-eb33cec02b5a4d4ba3ed0d63282034fd
Source dataset
uspto-grants-2014_07
Patent number
US08785489B2

Reaction notes

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