Imidazole → HCID 86687409, compound

HRID 1473362Notes

Reaction equation

HRID 1473362 reaction equation
CC(C)([O-])C.[K+].[NH:7]1[CH:11]=[CH:10][N:9]=[CH:8]1.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=1F.O1CCOCC1>O>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:17][C:18]=1[N:7]1[CH:11]=[CH:10][N:9]=[CH:8]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 312751,4-DioxaneHCID 1424144-Bromo-3-fluorobenzotrifluorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 86687409HCID 86687409, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

A microwave vial charged with potassium tert-butoxide (1.108 g, 9.88 mmol), 1H-imidazole (0.672 g, 9.88 mmol), 1-bromo-2-fluoro-4-(trifluoromethyl)benzene (1.180 ml, 8.23 mmol), and 10 mL dioxane was heated to 180° C. in the microwave for 2 hours. LC/MS showed mostly product, so the reaction mixture was poured into water and was extracted with DCM. The organics were dried over MgSO4 and concentrated. The crude residue was purified by silica gel column chromatography (0 to 100% EtOAc/heptane) yielding 1-(2-bromo-5-(trifluoromethyl)phenyl)-1H-imidazole (1.277 g, 4.39 mmol, 53.3% yield). m/z (ESI) 291.9 (M+H)+.

Workup

  1. extractionwas extracted with DCM
  2. dry with materialThe organics were dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude residue was purified by silica gel column chromatography (0 to 100% EtOAc/heptane)

Sources & evidence

ORD record
ord-5b6008d4138547a8acd0b4fc9ccbe250
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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