Imidazole → (3-Bromophenoxy)(tert-butyl)dimethylsilane

HRID 2359259Notes

Reaction equation

HRID 2359259 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.N1C=CN=C1.[CH3:14][C:15]([Si:18](Cl)([CH3:20])[CH3:19])([CH3:17])[CH3:16]>C(Cl)Cl>[Si:18]([O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)([C:15]([CH3:17])([CH3:16])[CH3:14])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 115633-BromophenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 11254705(3-Bromophenoxy)(tert-butyl)dimethylsilaneYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Bromophenol (6 mmol, 1.04 g), imidazole (10 mmol, 0.68 g) and TBDMSCl (6.6 mmol, 0.99 g) were dissolved in DCM (20 ml). The solution was allowed to stir at room temperature overnight. The solid generated during the reaction was filtered off and the solvent removed under reduced pressure. The resulting residue was subjected to flash chromatography (EtOAc/Hexanes=3%˜15%) giving compound 2 (1.56 g, 5.44 mmol, yield 91%). 1H NMR (CDCl3): δ 7.11-7.08 (m, 2H), 7.03-7.02 (m, 1H), 6.80-6.77 (m, 1H), 0.99 (s, 9H), 0.31 (s, 6H).

Workup

  1. filtrationwas filtered off
  2. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-28d5fc0052004aeea4e3fe2b0ca9ce92
Source dataset
uspto-grants-2014_04
Patent number
US08685979B2

Reaction notes

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