Imidazole → HCID 58319237, compound

HRID 2363133Notes

Reaction equation

HRID 2363133 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:12].N1C=CN=C1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>C(Cl)Cl.CCOC(C)=O>[C:21]([Si:18]([O:12][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([C:8]([F:10])([F:11])[F:9])[C:2]=1[Cl:1])([CH3:20])[CH3:19])([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 27366012-Chloro-3-(trifluoromethyl)phenol

Product 1

HCID 58319237HCID 58319237, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloro-3-trifluoromethyl-phenol (509 mg, 2.59 mmol) in CH2Cl2 (20 mL) was added imidazole (264 mg, 3.88 mmol). The mixture was stirred for 5 minutes, to which was added portionwise tert-butyldimethylsilyl chloride (467 g, 3.1 mmol). The mixture was stirred for 2 hours at room temperature and was diluted with EtOAc. The crude mixture was washed with 1N HCl, water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography to give tert-butyl-(2-chloro-3-trifluoromethyl-phenoxy)-dimethyl-silane (800 mg, 99%).

Workup

  1. stirringThe mixture was stirred for 2 hours at room temperature
  2. washThe crude mixture was washed with 1N HCl, water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-ee0b0d76cdc14e11904673219a2e4e9e
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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