Imidazole → HCID 67346559, compound

HRID 1518247Notes

Reaction equation

HRID 1518247 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 left stirring 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 colorless oil (94%), which was used without further characterization in the next reaction.

Workup

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

Sources & evidence

ORD record
ord-46649b618eff41dc8a2be2d8f73d2e6b
Source dataset
uspto-grants-2012_07
Patent number
US08232390B2

Reaction notes

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