Imidazole → Benzene, 1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-fluoro-5-methyl-

HRID 1020793Notes

Reaction equation

HRID 1020793 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].N1C=CN=C1>ClCCl>[C:13]([Si:10]([O:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([F:1])[CH:3]=1)([CH3:12])[CH3:11])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 35496693-Fluoro-5-methylphenol

Product 1

HCID 66726507Benzene, 1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-fluoro-5-methyl-Yield 102.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-fluoro-5-methylphenol (19.7 g, 156 mmol) and tert-butyldimethylsilyl chloride (25.9 g, 172 mmol) in dichloromethane (250 mL) was added imidazole (12.7 g, 187 mmol) at 0° C., and the mixture was stirred at room temperature for 2 h. The mixture was washed with water and brine and dried on anhydrous sodium sulfate. The solvent was removed in vacuo, and the residue was purified by silica gel chromatography (98:2 hexane/ethyl acetate) to give tert-butyl(3-fluoro-5-methylphenoxy)dimethylsilane (38.6 g, 100%).

Workup

  1. washThe mixture was washed with water and brine
  2. dry with materialdried on anhydrous sodium sulfate
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by silica gel chromatography (98:2 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-91ab94f0efc84d2b9889996de2634ab1
Source dataset
uspto-grants-2014_05
Patent number
US08716478B2

Reaction notes

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