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

HRID 45533Notes

Reaction equation

HRID 45533 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.

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-948e6bb28553492a8177c082e69c7e43
Source dataset
uspto-grants-2013_09
Patent number
US08541461B2

Reaction notes

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