Imidazole → HCID 58007486, compound

HRID 1094436Notes

Reaction equation

HRID 1094436 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:10])=[C:6]([CH:9]=1)[CH2:7][OH:8].N1C=CN=C1.[C:16]([Si:20]([CH3:23])([CH3:22])Cl)([CH3:19])([CH3:18])[CH3:17]>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:10])=[C:6]([CH:9]=1)[CH2:7][O:8][Si:20]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 5074766(5-Bromo-2-chlorophenyl)methanol

Product 1

HCID 58007486HCID 58007486, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-bromo-2-chlorobenzyl alcohol (3.00 g, 13.6 mmol) in DMF (10 ml) was added under a nitrogen atmosphere imidazole (2.89 g, 42.0 mmol). After cooling to 0° C. tert-butyldimethylchlorsilan (3.37 g, 22.3 mmol) was added and the reaction mixture was stirred for 18 h in a thawing ice bath. It was diluted with water (20 ml) and extracted with EtOAc (20 ml). The aqueous layer was extracted with ethyl acetate (20 ml) and the organic layers were washed with water (20 ml) and brine (20 ml) and were dried over sodium sulfate. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 80:20) afforded the title compound (4.35 g, 96%) as a colorless liquid. MS m/e: 279.0 [M−tBu]+.

Workup

  1. additionwas added
  2. extractionextracted with EtOAc (20 ml)
  3. extractionThe aqueous layer was extracted with ethyl acetate (20 ml)
  4. washthe organic layers were washed with water (20 ml) and brine (20 ml)
  5. dry with materialwere dried over sodium sulfate
  6. concentrationConcentration and purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 80:20)

Sources & evidence

ORD record
ord-e63b6f06b3714e9d908fe68710b253ed
Source dataset
uspto-grants-2012_03
Patent number
US08133909B2

Reaction notes

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