2,6-Lutidine → HCID 22121423, compound

HRID 2167703Notes

Reaction equation

HRID 2167703 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[Br:32]N1C(=O)CCC1=O>O.C(Cl)(Cl)Cl>[Br:32][CH2:10][C:9]([C:3]1[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[F:1])=[O:11]

Participants

7

Reactant 4

HCID 79372,6-LutidineHCID 65367Trimethylsilyl triflateHCID 67184N-bromobutanimideHCID 27784842'-Fluoro-4'-methylacetophenone

Product 1

HCID 22121423HCID 22121423, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a chloroform (7.5 mL) solution of 1-(2-fluoro-4-methylphenyl)ethanone (0.50 g), under ice cooling in a nitrogen atmosphere, 2,6-lutidine (0.65 mL) and trimethylsilyl trifluoromethanesulfonate (0.71 mL) were added, and the resultant was stirred for 30 minutes. Then, N-bromosuccinimide (0.64 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 10 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 (0.72 g) as a white solid.

Workup

  1. stirringthe resultant was stirred for 30 minutes under ice cooling
  2. stirringthe resultant was stirred for 10 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-d8714d694d1841708084b9497442d15f
Source dataset
uspto-grants-2015_06
Patent number
US09045466B2

Reaction notes

Loading…