2-(Trimethylsilyl)ethanol → (2-(3-Chloro-4-(trifluoromethyl)phenoxy)ethyl)trimethylsilane

HRID 2359292Notes

Reaction equation

HRID 2359292 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].[CH3:13][Si:14]([CH3:19])([CH3:18])[CH2:15][CH2:16][OH:17].[H-].[Na+].S([O-])(O)(=O)=O.[K+]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10])[O:17][CH2:16][CH2:15][Si:14]([CH3:19])([CH3:18])[CH3:13]

Participants

6

Reactant 4

HCID 180132-(Trimethylsilyl)ethanolHCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 232358632-Chloro-4-fluoro-1-(trifluoromethyl)benzene

Product 1

HCID 58046336(2-(3-Chloro-4-(trifluoromethyl)phenoxy)ethyl)trimethylsilaneYield 870.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-chloro-4-fluoro-(trifluoromethyl)benzene (2.39 g, 1.2 mmol) and 2-(trimethylsilyl)ethanol (2.13 g, 1.8 mmol) in anhydrous tetrahydrofuran (100 mL) was added sodium hydride (0.72 g, 1.8 mmol, 60% in mineral oil). The resulting mixture was stirred at room temperature for 18 hours under nitrogen. The reaction mixture was poured onto water and acidified with aqueous potassium hydrogen sulfate and extracted with ethyl acetate (3×30 mL), dried (MgSO4), filtered and concentrated in vacuo to afford 3.1 g (87%) of the title compound as a colourless oil.

Workup

  1. additionThe reaction mixture was poured onto water
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e66e22e37c3f47ce8eda7d0d629d7493
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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