Water → 4-Bromo-2-(4-fluorophenyl)-1-(2-trimethylsilanyl-ethoxymethyl)imidazole

HRID 1369413Notes

Reaction equation

HRID 1369413 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[N:5]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1Br.C(O)(C)C.O>C1COCC1>[Br:1][C:2]1[N:3]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[N:5]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3776IsopropanolHCID 185159564,5-dibromo-2-(4-fluorophenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole

Product 1

HCID 185159744-Bromo-2-(4-fluorophenyl)-1-(2-trimethylsilanyl-ethoxymethyl)imidazoleYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4,5-Dibromo-2-(4-fluorophenyl)-1-(2-trimethylsilanyl-ethoxymethyl)imidazole (10.8 g; 25 mmol) are dissolved in THF (108 ml) and cooled to −78 C under argon. N-BuLi (15.6 ml; 1.6 M) is added under stirring within 15 min. After 30 min at −78 C, isopropanol (7.8 ml; 0.1 mol) is introduced dropwise and the mixture warmed to room temperature. Water is added to the reaction mixture and the aqueous phase extracted three times with ethyl acetate. The combined organic phases are washed with saturated NaCl-solution, dried over Na2SO4, filtered and evaporated to dryness, yielding the title compound as colorless oil (9.1 g; 95%).

Workup

  1. temperaturecooled to −78 C under argon
  2. extractionthe aqueous phase extracted three times with ethyl acetate
  3. washThe combined organic phases are washed with saturated NaCl-solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-27ec40cfa6434e8c8dd5011caf528aad
Source dataset
uspto-grants-2003_06
Patent number
US06579874B2

Reaction notes

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