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

HRID 924740Notes

Reaction equation

HRID 924740 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-2240170336c84eb7af44f797c34ecb8c
Source dataset
uspto-grants-2016_03
Patent number
US09283226B2

Reaction notes

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