Imidazole → HCID 67346559, compound

HRID 1669428Notes

Reaction equation

HRID 1669428 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][OH:11].N1C=CN=C1.[CH:17]([Si:20](Cl)([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])([CH3:19])[CH3:18]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][O:11][Si:20]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:17]([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 10867706(2-Bromo-5-methoxyphenyl)methanol

Product 1

HCID 67346559HCID 67346559, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2-Bromo-5-methoxyphenyl)methanol (1 eq) was dissolved in anhydrous DMF (1.1M solution) and imidazole (1.05 eq) was added. To the stirred solution triisopropylsilyl chloride (1.1 eq) was added and the resulting mixture was stirred at RT for 8 h. All volatiles were evaporated in vacuo and the residual material was filtered with PE/EtOAc (9:1) over a pad of silica gel. After evaporation in vacuo the product was obtained as a colourless oil (94%), which was used without further characterization in the next reaction.

Workup

  1. customAll volatiles were evaporated in vacuo
  2. filtrationthe residual material was filtered with PE/EtOAc (9:1) over a pad of silica gel
  3. customAfter evaporation in vacuo the product

Sources & evidence

ORD record
ord-a0c41e985ad54374be12de9a9bfa83de
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

Loading…