Imidazole → (3,5-Dichlorophenoxy)tris(propan-2-YL)silane

HRID 63723

Reaction equation

HRID 63723 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([Cl:8])[CH:7]=1.N1C=CN=C1.[CH:15]([Si:18]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])Cl)([CH3:17])[CH3:16].CN(C=O)C>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([Cl:8])[CH:7]=1)[O:9][Si:18]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:15]([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 115713,5-DichlorophenolHCID 139400Triisopropylsilyl chloride

Product 1

HCID 21594466(3,5-Dichlorophenoxy)tris(propan-2-YL)silaneYield 97.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 3,5-dichlorophenol (16.3 g, 100 mmol), imidazole (14.98 g, 220 mmol), and triisopropylchlorosilane (21.21 g, 110 mmol) was added DMF (200 mL) at room temperature. The resulting brown solution was stirred for 15 h and then it was diluted with water (500 mL). The organic compound was extracted into ethyl acetate (2×100 mL) and the combined organic layer was washed with brine solution and dried over anhydrous MgSO4. Filtration and concentration gave the crude residue which was purified using an ISCO (400 g) column chromatography to obtain 31.1 g (97%) of (3,5-dichlorophenoxy)-triisopropylsilane as a colorless oil. EI(+)-HRMS m/e calcd. for C15H24Cl2OSi (M)+ 318.0973, obsd. 318.0971.

Workup

  1. extractionThe organic compound was extracted into ethyl acetate (2×100 mL)
  2. washthe combined organic layer was washed with brine solution
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationFiltration and concentration
  5. customgave the crude residue which
  6. customwas purified

Sources & evidence

ORD record
ord-a17d2cdcd2c949aab7f4b4f023a6eabf
Source dataset
uspto-grants-2016_09
Patent number
US09447035B2

Linked notes

Loading…