Imidazole → 2-Bromo-5-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-chloro-phenylamine

HRID 1691826Notes

Reaction equation

HRID 1691826 reaction equation
[NH2:1][C:2]1[C:3]([Br:12])=[CH:4][C:5]([Cl:11])=[C:6]([CH:8]([OH:10])[CH3:9])[CH:7]=1.[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].N1C=CN=C1.O>CN(C=O)C>[Br:12][C:3]1[CH:4]=[C:5]([Cl:11])[C:6]([CH:8]([O:10][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH3:9])=[CH:7][C:2]=1[NH2:1]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 593778031-(5-Amino-4-bromo-2-chloro-phenyl)-ethanol

Product 1

HCID 593778892-Bromo-5-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-chloro-phenylamineYield 92.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(5-amino-4-bromo-2-chloro-phenyl)-ethanol (0.195 g, 0.778 mmol) in DMF (3 ml) was added tert-butyl-dimethylsilyl chloride (0.152 g, 1.011 mmol) and imidazole (0.069 g, 1.011 mmol). The mixture was stirred at room temperature for six hours. Water was added and the mixture was extracted with EtOAc. The combined organic extracts were washed with water and brine, dried over MgSO4, filtered and concentrated to dryness under reduced pressure. Purification of the residue by flash chromatography (hex:EtOAc/9:1) gave 2-bromo-5-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-chloro-phenylamine (0.262 g, 92%) as a clear oil.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washThe combined organic extracts were washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure
  6. customPurification of the residue by flash chromatography (hex:EtOAc/9:1)

Sources & evidence

ORD record
ord-753f02ef65b040cd8e341783aeb04dd6
Source dataset
uspto-grants-2012_04
Patent number
US08153809B2

Reaction notes

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