Imidazole → HCID 86687409, compound

HRID 2172285Notes

Reaction equation

HRID 2172285 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>CN(C=O)C.C(Cl)Cl>[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 3

HCID 795ImidazoleHCID 1424144-Bromo-3-fluorobenzotrifluorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 86687409HCID 86687409, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

A microwave vial charged with a solution of potassium tert-butoxide (0.462 g, 4.12 mmol), imidazole (0.280 g, 4.12 mmol), and 1-bromo-2-fluoro-4-(trifluoromethyl)benzene (1.000 g, 4.12 mmol) in 2 mL DMF was heated to 150° C. in an oil bath overnight. The reaction mixture was diluted with DCM, filtered through a syringe filter, and concentrated. Purification of the resulting residue by silica gel column chromatography (0 to 100% EtOAc/heptane) gave 1-(2-bromo-5-(trifluoromethyl)phenyl)-1H-imidazole (0.720 g, 2.474 mmol). [M+H]+=291.0

Workup

  1. filtrationfiltered through a syringe
  2. filtrationfilter
  3. concentrationconcentrated
  4. customPurification of the resulting residue by silica gel column chromatography (0 to 100% EtOAc/heptane)

Sources & evidence

ORD record
ord-d71d91952a684a0e978a3f32f68ba3cd
Source dataset
uspto-grants-2015_06
Patent number
US09051311B2

Reaction notes

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