Imidazole → (2-Bromobenzyloxy)tert-butyldimethylsilane

HRID 2196441Notes

Reaction equation

HRID 2196441 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][OH:9].N1C=CN=C1.[Cl-].[C:16]([SiH:20]([CH3:22])[CH3:21])([CH3:19])([CH3:18])[CH3:17]>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][Si:20]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 728502-Bromobenzyl alcoholHCID 131722836Tert-butyldimethylsilane chloride

Product 1

HCID 13424900(2-Bromobenzyloxy)tert-butyldimethylsilaneYield 82.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.0 g of (2-bromophenyl)methanol are placed in a round-bottomed flask and dissolved in 100 ml of tetrahydrofuran. 1.1 g of 1H-imidazole are added thereto, followed by 2.1 g of tert-butyldimethylsilane chloride, and the mixture is left to stir at ambient temperature for 48 hours. The reaction mixture is then hydrolysed with water, and the organic phase, which has been extracted with ethyl acetate, is separated, dried over magnesium sulphate and concentrated under reduced pressure. The residue obtained is purified by silica gel chromatography, elution being carried out with a heptane/ethyl acetate mixture. 2.66 g of compound are obtained.

Workup

  1. waitthe mixture is left
  2. extractionhydrolysed with water, and the organic phase, which has been extracted with ethyl acetate
  3. customis separated
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. customis purified by silica gel chromatography, elution

Sources & evidence

ORD record
ord-31c87749347749b681e3724889802906
Source dataset
uspto-grants-2012_12
Patent number
US08338451B2

Reaction notes

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