Imidazole → HCID 58007486, compound

HRID 406400Notes

Reaction equation

HRID 406400 reaction equation
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[Br:14][C:15]1[CH:16]=[CH:17][C:18]([Cl:23])=[C:19]([CH2:21][OH:22])[CH:20]=1>CN(C=O)C.C(OCC)(=O)C>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([Cl:23])=[C:19]([CH:20]=1)[CH2:21][O:22][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 5074766(5-Bromo-2-chlorophenyl)methanol

Product 1

HCID 58007486HCID 58007486, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Imidazole (5.22 g) and tert-butyldimethylsilyl chloride (8.64 g) were added to a solution of (5-bromo-2-chlorophenyl)methanol (8.47 g) in DMF (80 ml). The reaction mixture was stirred at room temperature overnight. The mixture was diluted with ethyl acetate and washed twice with water. The aqueous layer was again extracted with ethyl acetate. The combined organic layer was washed with brine and dried over anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound (12.6 g).

Workup

  1. washwashed twice with water
  2. extractionThe aqueous layer was again extracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5eba45b7fce2423d9641934daf9dc6ad
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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