Sodium hydride → (4-Bromo-3-methoxyphenoxy)triisopropylsilane

HRID 1716793Notes

Reaction equation

HRID 1716793 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[O:9][CH3:10].[H-].[Na+].[CH:13]([Si:16](Cl)([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])([CH3:15])[CH3:14].C1([O-])C=CC=CC=1>C1COCC1.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][Si:16]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:13]([CH3:15])[CH3:14])=[CH:4][C:3]=1[O:9][CH3:10]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 119047PhenolateHCID 139400Triisopropylsilyl chlorideHCID 3479554-Bromo-3-methoxyphenol

Product 1

HCID 11314363(4-Bromo-3-methoxyphenoxy)triisopropylsilaneYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 4-bromo-3-methoxyphenol (5.00 g, 24.6 mmol, Chontech) in THF (50 ml) was added dropwise to a suspension of sodium hydride (1.08 g, 60% dispersion in mineral oil, 27 mmol) in THF (100 ml) over 10 min while cooling in ice. The reaction mixture was stirred at 0° C. for 30 min and then at room temperature for 60 min. Triisopropylsilyl chloride was added dropwise to the phenolate solution, and the reaction mixture was stirred at room temperature for 60 min. Water was added to the mixture while cooling in ice, and it was then extracted several times with ethyl acetate. The combined organic phase was washed with saturated sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. Purification by chromatography on silica gel (mobile phase: 2-10% gradient of ethyl acetate in dichloromethane) afforded 8.67 g (98%) of the desired product.

Workup

  1. temperaturewhile cooling in ice
  2. waitat room temperature for 60 min
  3. stirringthe reaction mixture was stirred at room temperature for 60 min
  4. temperaturewhile cooling in ice
  5. extractionit was then extracted several times with ethyl acetate
  6. washThe combined organic phase was washed with saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customPurification by chromatography on silica gel (mobile phase: 2-10% gradient of ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-dad151d2c68e4d639b633be778f1ba95
Source dataset
uspto-grants-2010_09
Patent number
US07803834B2

Reaction notes

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