Imidazole → HCID 58149395, compound

HRID 449836Notes

Reaction equation

HRID 449836 reaction equation
[C:1]([Si:5]([CH3:8])([CH3:7])Cl)([CH3:4])([CH3:3])[CH3:2].[F:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([CH3:17])[CH:11]=1.N1C=CN=C1>CN(C)C=O.CCOCC>[C:1]([Si:5]([O:16][C:13]1[CH:14]=[CH:15][C:10]([F:9])=[CH:11][C:12]=1[CH3:17])([CH3:8])[CH3:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 1362954-Fluoro-2-methylphenol

Product 1

HCID 58149395HCID 58149395, compoundYield 101.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

t-Butyldimethylchlorosilane (14.34 g, 93.24 mmol) is combined with 4-fluoro-2-methylphenol (10.00 g, 77.70 mmol) and 1H-imidazole (13.32 g, 194.24 mmol) in dimethylformamide (100 mL) and stirred at room temperature overnight. The reaction is diluted with ether (200 mL) and washed with water (2×100 mL) and brine. The organic portion is dried with sodium sulfate, filtered, and concentrated to afford 18.9 g (100%) of the title compound. GC-ES m/z 240 [M]+, TR=4.06 min.

Workup

  1. washwashed with water (2×100 mL) and brine
  2. dry with materialThe organic portion is dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b0401d676f5245aeb50b8f4d14116f64
Source dataset
uspto-grants-2013_07
Patent number
US08486943B2

Reaction notes

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