HCID 178418785, compound → HCID 178519737, compound

HRID 1694791Notes

Reaction equation

HRID 1694791 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([O:8]C)=O)[N:3]=[CH:2]1.[F:10][C:11]1[CH:12]=[C:13]([Mg]Br)[CH:14]=[C:15]([F:17])[CH:16]=1>O1CCCC1>[F:10][C:11]1[CH:12]=[C:13]([C:6]([C:13]2[CH:12]=[C:11]([F:10])[CH:16]=[C:15]([F:17])[CH:14]=2)([C:4]2[N:3]=[CH:2][NH:1][CH:5]=2)[OH:8])[CH:14]=[C:15]([F:17])[CH:16]=1

Participants

4

Reactant 2

HCID 178418785HCID 178418785, compoundHCID 178505930HCID 178505930, compound

Product 1

HCID 178519737HCID 178519737, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-imidazolecarboxylate 0.80 g (6.34 mmol) was placed in a flask and under argon 50 ml (25 mmol) of a 0.5M 3,5-difluorophenylmagnesium bromide solution in tetrahydrofuran were added. The mixture was refluxed for 2 hours and then most of the solvent was evaporated. Water was added with cooling, and the mixture was extracted twice with ethyl acetate. The combined organic extracts were concentrated and the residue was purified by flash chromatography (silica gel, heptane/ethyl acetate 8:2) to yield 1.5 g (73%) of bis-(3,5-difluoro-phenyl)-(1H-imidazol-4-yl)-methanol as a white solid; MS (ISP): 305.1 ((M-OH)+); 323.4 ((M+H)+.).

Workup

  1. additionwere added
  2. temperatureThe mixture was refluxed for 2 hours
  3. custommost of the solvent was evaporated
  4. additionWater was added
  5. temperaturewith cooling
  6. extractionthe mixture was extracted twice with ethyl acetate
  7. concentrationThe combined organic extracts were concentrated
  8. customthe residue was purified by flash chromatography (silica gel, heptane/ethyl acetate 8:2)

Sources & evidence

ORD record
ord-6ef5890e7be245cfab2ca44b14ad7fae
Source dataset
uspto-grants-2012_04
Patent number
US08158668B2

Reaction notes

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