Imidazole → 1-(4-Bromo-phenyl)-3-imidazol-1-yl-propan-1-ol

HRID 2361806Notes

Reaction equation

HRID 2361806 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:12])[CH2:9][CH2:10]Cl)=[CH:4][CH:3]=1.[NH:13]1[CH:17]=[CH:16][N:15]=[CH:14]1>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:12])[CH2:9][CH2:10][N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 108006384-Bromo-alpha-(2-chloroethyl)benzenemethanol

Product 1

HCID 214153621-(4-Bromo-phenyl)-3-imidazol-1-yl-propan-1-olYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(4-Bromo-phenyl)-3-chloro-propan-1-ol* (1.5 g, 6.01 mmol) and imidazole (1.23 g, 18.03 mmol) in dimethylformamide (18 ml) was heated at 100° C. for 18 hrs then partitioned between water and ethyl acetate. The organic extracts were combined, dried (MgSO4), filtered, concentrated and purified by column chromatography (SiO2), eluting with methanol:dichloromethane (2:98) to methanol:dichloromethane (6:94) to afford the title compound (0.75 g, 44% yield). LC/MS: (PS-B3) Rt 2.48 [M+H]+ 281.14, 283.11. *This starting material can be made by the method described in Example 43A.

Workup

  1. customthen partitioned between water and ethyl acetate
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by column chromatography (SiO2)
  6. washeluting with methanol:dichloromethane (2:98) to methanol:dichloromethane (6:94)

Sources & evidence

ORD record
ord-0d5c340fe4a9471b8f224d516c5b3118
Source dataset
uspto-grants-2014_04
Patent number
US08691806B2

Reaction notes

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