Imidazole → HCID 86687409, compound

HRID 2172296Notes

Reaction equation

HRID 2172296 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[O-:6]CC.[Na+].[Br:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=1F.O>O1CCOCC1.CO>[NH4+:1].[OH-:6].[Br:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:15][C:16]=1[N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

8

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 1424144-Bromo-3-fluorobenzotrifluorideHCID 2723922Sodium ethoxide

Product 2

HCID 14923Ammonium HydroxideYield 0.1%HCID 86687409HCID 86687409, compoundYield 44.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 1H-imidazole (0.420 g, 6.17 mmol) in 12 mL dioxane was treated with sodium ethoxide (0.441 g, 6.48 mmol) and was allowed to stir for 30 minutes. 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene (0.885 ml, 6.17 mmol) was added and the reaction mixture was heated to 120° C. in a sealed vial overnight. The reaction mixture was poured into water and was extracted with EtOAc. The organics were concentrated and purified directly by reverse phase column chromatography [RediSep Gold C-18 100 g (Teledyne Isco, Lincoln, Nebr.), 10 to 100% (0.1% NH4OH in MeOH)/(0.1% NH4OH in water)] yielding 1-(2-bromo-5-(trifluoromethyl)phenyl)-1H-imidazole (0.400 g, 1.374 mmol).

Workup

  1. extractionwas extracted with EtOAc
  2. concentrationThe organics were concentrated
  3. custompurified directly by reverse phase column chromatography [RediSep Gold

Sources & evidence

ORD record
ord-f3ea4bdf3c9046368d21e37f68bbae8c
Source dataset
uspto-grants-2015_06
Patent number
US09051311B2

Reaction notes

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