Imidazole → Tert-butyl(2,4-dichlorophenoxy)dimethylsilane

HRID 253432Notes

Reaction equation

HRID 253432 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].N1C=CN=C1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].O>CN(C)C=O>[C:18]([Si:15]([O:9][C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])([CH3:17])[CH3:16])([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 84492,4-DichlorophenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 59803885Tert-butyl(2,4-dichlorophenoxy)dimethylsilane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2,4-dichloro-phenol, (112, 4.80 g, 0.0294 mol) in N,N-dimethylformamide (100.0 mL) were added 1H-imidazole (5.21 g, 0.0766 mol) and tert-butyldimethylsilyl chloride (5.33 g, 0.0353 mol). The reaction was stirred at room temperature overnight. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 15% to 50% ethyl acetate in hexane to give a colorless oil (113, 7.10 g, 87.0%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 15% to 50% ethyl acetate in hexane
  7. customto give a colorless oil (113, 7.10 g, 87.0%)

Sources & evidence

ORD record
ord-fc54015df25d4480b68d968b935b59e8
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

Loading…