2,4,5-Tribromoimidazole → 2,4,5-tribromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-Imidazole

HRID 2393568Notes

Reaction equation

HRID 2393568 reaction equation
[Br:1][C:2]1[NH:6][C:5]([Br:7])=[N:4][C:3]=1[Br:8].[H-].[Na+].[CH3:11][Si:12]([CH3:19])([CH3:18])[CH2:13][CH2:14][O:15][CH2:16]Cl.[NH4+].[Cl-]>C1COCC1>[Br:7][C:5]1[N:4]([CH2:16][O:15][CH2:14][CH2:13][Si:12]([CH3:19])([CH3:18])[CH3:11])[C:3]([Br:8])=[C:2]([Br:1])[N:6]=1

Participants

6

Reactant 4

HCID 162532,4,5-TribromoimidazoleHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 109062032,4,5-tribromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-Imidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.04 g of tribromoimidazole is dissolved in 20 cm3 of anhydrous THF. 550 mg of NaH at 50% in oil is added in small portions. After 20 minutes at ambient temperature, 1.95 ml of 2-(trimethylsilyl) ethoxy methyl chloride is added. After 30 minutes at ambient temperature, the reaction medium is hydrolyzed with a saturated solution of NH4Cl, followed by extraction with AcOEt, drying and evaporating to dryness. Chromatography is carried out on silica eluting with cyclohexane/AcOEt (9-1) and 4.2 g of expected product (oil) is recovered.

Workup

  1. waitAfter 30 minutes at ambient temperature
  2. extractionfollowed by extraction with AcOEt
  3. customdrying
  4. customevaporating to dryness
  5. customis recovered

Sources & evidence

ORD record
ord-12512e8e0eaf40f8ae14068100a7d38b
Source dataset
uspto-grants-1998_09
Patent number
US05807878

Reaction notes

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