Benzyl Bromide → Benzyl-2-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

HRID 1409437Notes

Reaction equation

HRID 1409437 reaction equation
[Br:1][C:2]1[N:3]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[CH:4]=[C:5]([C:7]([OH:9])=[O:8])[N:6]=1.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(#N)C.[Ag]=O>[CH2:18]([O:8][C:7]([C:5]1[N:6]=[C:2]([Br:1])[N:3]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[CH:4]=1)=[O:9])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 709813012-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylic acid

Product 1

HCID 70980971Benzyl-2-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6342AcetonitrileSolvent

Procedure

Silver oxide (12.7 g, 54.8 mmol) was added to a solution of 2-bromo-1-((2-(trimethyl-silyl)ethoxy)methyl)-1H-imidazole-4-carboxylic acid (11.7 g, 36.5 mmol) in ACN (200 ml) and stirred at RT for 10 min. Benzyl bromide (4.2 ml, 36.5 mmol) was added to the mixture and stirred at RT for 12 h. The reaction mixture was filtered through a celite bed and the filtrate was concentrated under reduced pressure. The product was purified by flash chromatography. Yield 10 g. 1H-NMR (400 MHz; CDCl3): δ −0.04 (s, 9H), 0.92 (t, 2H), 3.54 (t, 2H), 5.29 (s, 2H), 5.35 (s, 2H), 7.30-7.44 (m, 5H), 7.76 (s, 1H).

Workup

  1. stirringstirred at RT for 12 h
  2. filtrationThe reaction mixture was filtered through a celite bed
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-fba620e6f9204df0aeadde4a880b86bd
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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