Imidazole → 4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1-fluoro-2-methylbenzene

HRID 899240Notes

Reaction equation

HRID 899240 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].N1C=CN=C1.[C:15]([Si:19](Cl)([CH3:21])[CH3:20])([CH3:18])([CH3:17])[CH3:16]>CN(C)C=O>[C:15]([Si:19]([O:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([CH3:9])[CH:4]=1)([CH3:21])[CH3:20])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 27373944-Fluoro-3-methylphenol

Product 1

HCID 580060724-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1-fluoro-2-methylbenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-fluoro-3-methylphenol (15 g, 0.12 mol) and imidazole (18 g, 0.26 mol) in N,N-dimethylformamide (100 mL) was added tert-butyl(chloro)dimethylsilane (20 g, 0.13 mol) at 0° C. The reaction mixture was stirred at room temperature for 20 h, and quenched by the addition of water. The aqueous layer was extracted with diethyl ether (400 mL). The combined organic layers were washed with water and brine, dried over magnesium sulfate, and evaporated to afford 30 g (quant.) of the title compound as a yellow oil:

Workup

  1. customquenched by the addition of water
  2. extractionThe aqueous layer was extracted with diethyl ether (400 mL)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-88e5f806562e4c88b0fef75c8c67bc3b
Source dataset
uspto-grants-2008_04
Patent number
US07354925B2

Reaction notes

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