Imidazole → (4-Bromo-2,6-dimethylphenoxy)triisopropylsilane

HRID 1171005Notes

Reaction equation

HRID 1171005 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=1.N1C=CN=C1.[CH:16]([Si:19](Cl)([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])([CH3:18])[CH3:17]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][Si:19]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:16]([CH3:18])[CH3:17])=[C:4]([CH3:10])[CH:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 169194-Bromo-2,6-dimethylphenolHCID 139400Triisopropylsilyl chloride

Product 1

HCID 66642823(4-Bromo-2,6-dimethylphenoxy)triisopropylsilaneYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 4-bromo-2,6-dimethylphenol (6 g, 29.85 mmol) in CH2Cl2 (80 mL) at 0° C. was added imidazole (4.1 g, 59.70 mmol) and triisopropylsilyl chloride (7.1 mL, 32.84 mmol). The reaction mixture was stirred at room temperature for 16 hrs. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel; eluting with ethyl acetate-hexanes (1:9) to afford (4-bromo-2,6-dimethylphenoxy)triisopropylsilane as a colorless oil (1.6 g, 15%): 1H NMR (300 MHz, DMSO-d6): δ 7.19 (s, 2 H), 2.20 (s, 6 H), 1.29 (m, 3 H), 1.10 (d, J=7.2 Hz, 18 H). TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=ethyl acetate-hexanes (5:95); Rf=0.70.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel
  7. washeluting with ethyl acetate-hexanes (1:9)

Sources & evidence

ORD record
ord-9f2d5c59bbfd495d907c8be934ae1f59
Source dataset
uspto-grants-2010_11
Patent number
US07829552B2

Reaction notes

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