Imidazole → HCID 58007486, compound

HRID 561787Notes

Reaction equation

HRID 561787 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:10])=[C:6]([CH2:8][OH:9])[CH:7]=1.N1C=CN=C1.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:10])=[C:6]([CH:7]=1)[CH2:8][O:9][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

5

Reactant 3

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

Product 1

HCID 58007486HCID 58007486, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (5-bromo-2-chlorophenyl)methanol from the previous step (1 eq.) in DMF (0.25 M) was added imidazole (1.2 eq.) and tert-butyldimethylsilyl chloride (1.1 eq.). The resulting solution was stirred at RT for 3 h. The reaction mixture was quenched with sat. aq. NH4Cl and extracted with ether. The combined organic extracts were washed further with aq. 10% HCl, sat. aq. NaHCO3, and brine. Concentration of the organic extracts in vacuo afforded an orange oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc) afforded the title compound as a light yellow oil.

Workup

  1. customThe reaction mixture was quenched with sat. aq. NH4Cl
  2. extractionextracted with ether
  3. washThe combined organic extracts were washed further with aq. 10% HCl, sat. aq. NaHCO3, and brine
  4. customConcentration of the organic extracts in vacuo afforded an orange oil
  5. customPurification of the crude product
  6. customthus obtained by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-b6496fd24ff24f81998771fecd343191
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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