Imidazole → HCID 22048157, compound

HRID 2036138Notes

Reaction equation

HRID 2036138 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([OH:9])=[C:4]([F:10])[CH:3]=1.N1C=CN=C1.[C:16]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])([CH3:18])[CH3:17]>ClCCl.O>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([O:9][Si:20]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:22])[CH3:21])=[C:4]([F:10])[CH:3]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 27362924-Bromo-2,6-difluorophenol

Product 1

HCID 22048157HCID 22048157, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4-Bromo-2,6-difluorophenol D1c (5.0 g, 24 mmol) is dissolved in dichloromethane (50 mL) and treated with imidazole (2.28 g, 33.5 mmol). The colorless solution is treated in portions, with stirring, with tert-butylchlorodimethylsilane (4 g, 26 mmol). The mixture is stirred at room temperature overnight. The mixture is diluted with water (150 mL) and extracted with dichloromethane. The organic phase is washed with sat. NH4Cl solution, dried over Na2SO4 and concentrated in vacuo. Purification of the crude material by flash chromatography (hexanes/ethyl acetate gradient) affords (4-bromo-2,6-difluorophenoxy)(tert-butyl)dimethylsilane D1d as a clear oil. 1H-NMR (400 MHz, CDCl3) δ=7.05 (d, J=7.2 Hz, 2H), 1.00 (s, 9H), 0.19 (s, 6H); no MS spectrum could be obtained.

Workup

  1. additionThe colorless solution is treated in portions
  2. extractionextracted with dichloromethane
  3. washThe organic phase is washed with sat. NH4Cl solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification of the crude material by flash chromatography (hexanes/ethyl acetate gradient)

Sources & evidence

ORD record
ord-f6e02fa47975417188d1f3151343175f
Source dataset
uspto-grants-2013_11
Patent number
US08575168B2

Reaction notes

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