2,6-Lutidine → HCID 80115392, compound

HRID 2167702Notes

Reaction equation

HRID 2167702 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([F:9])=[CH:4][C:3]=1[C:10](=[O:12])[CH3:11].N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[Br:33]N1C(=O)CCC1=O>O.C(Cl)(Cl)Cl>[Br:33][CH2:11][C:10]([C:3]1[CH:4]=[C:5]([F:9])[C:6]([CH3:8])=[CH:7][C:2]=1[F:1])=[O:12]

Participants

7

Reactant 4

HCID 79372,6-LutidineHCID 65367Trimethylsilyl triflateHCID 67184N-bromobutanimideHCID 20785250HCID 20785250, compound

Product 1

HCID 80115392HCID 80115392, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a chloroform (3.5 mL) solution of 1-(2,5-difluoro-4-methylphenyl)ethanone (0.23 g), under ice cooling in a nitrogen atmosphere, 2,6-lutidine (0.27 mL) and trimethylsilyl trifluoromethanesulfonate (0.32 mL) were added, and the resultant was stirred for 30 minutes. Then, N-bromosuccinimide (0.27 g) was added thereto, and the resultant was stirred for 30 minutes under ice cooling. Water was added to the reaction solution, and the resultant was stirred for 15 minutes, followed by extraction with chloroform. An organic layer was separated using a phase separator, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (OH-type silica gel; hexane/ethyl acetate-gradient elution=99/1→95/5) to obtain the title compound (0.31 g) as a white solid.

Workup

  1. stirringthe resultant was stirred for 30 minutes under ice cooling
  2. stirringthe resultant was stirred for 15 minutes
  3. extractionfollowed by extraction with chloroform
  4. customAn organic layer was separated
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (OH-type silica gel; hexane/ethyl acetate-gradient elution=99/1→95/5)

Sources & evidence

ORD record
ord-e902a80195f64551abb7c9d21f343797
Source dataset
uspto-grants-2015_06
Patent number
US09045466B2

Reaction notes

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