Imidazole → HCID 19603523, compound

HRID 1604532Notes

Reaction equation

HRID 1604532 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.[CH:15]([Si:18](Cl)([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])([CH3:17])[CH3:16]>CN(C)C=O.O>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([O:9][Si:18]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:15]([CH3:17])[CH3:16])=[C:2]([Cl:1])[CH:7]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 84492,4-DichlorophenolHCID 139400Triisopropylsilyl chloride

Product 1

HCID 19603523HCID 19603523, compoundYield 81.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2,4-dichlorophenol (3.20 g) and imidazole (2.67 g) in dimethylformamide (30 ml) was added triisopropylsilyl chloride (3.97 g) in water bath under nitrogen atmosphere, and the mixture was stirred for 3 hours under the same condition. The mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (n-hexane) to give 1,3-dichloro-4-triisopropylsilyloxybenzene (5.12 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography (n-hexane)

Sources & evidence

ORD record
ord-fb1dfc6ff76946a7bb338a976b7c0d78
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

Loading…