Imidazole → (3-Bromo-4-fluorophenoxy)(tert-butyl)dimethylsilane

HRID 2404582Notes

Reaction equation

HRID 2404582 reaction equation
[CH3:1][C:2]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])[CH3:3].N1C=CN=C1.[Br:14][C:15]1[CH:16]=[C:17]([OH:22])[CH:18]=[CH:19][C:20]=1[F:21]>C(Cl)Cl>[Br:14][C:15]1[CH:16]=[C:17]([CH:18]=[CH:19][C:20]=1[F:21])[O:22][Si:5]([C:2]([CH3:4])([CH3:3])[CH3:1])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 27833813-Bromo-4-Fluorophenol

Product 1

HCID 59315494(3-Bromo-4-fluorophenoxy)(tert-butyl)dimethylsilaneYield 102.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add TBSCl (3.37 g, 22.37 mmol) and imidazole (1.9 g, 27.96 mmol) to a solution of 3-bromo-4-fluoro-phenol (3.56 g 18.64 mmol) in CH2Cl2 (60 ml). Stir the solution at ambient temperature for 3 hours. Quench the reaction with water (30 mL). Extract the aqueous layer with CH2Cl2 (30 mL×3). The combined organic layers are washed with brine, dried over Na2SO4, concentrated under vacuum. The residue is purified by silica gel chromatography (petroleum ether) to give (3-bromo-4-fluoro-phenoxy)-tert-butyl-dimethyl-silane as colorless oil (5.81 g, 99%), MS (m/z): 303 (M−1).

Workup

  1. customQuench
  2. customthe reaction with water (30 mL)
  3. extractionExtract the aqueous layer with CH2Cl2 (30 mL×3)
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum
  7. customThe residue is purified by silica gel chromatography (petroleum ether)

Sources & evidence

ORD record
ord-08881c2d678245b8b9ac2ce65c334535
Source dataset
uspto-grants-2014_08
Patent number
US08802728B2

Reaction notes

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