Pyridine → HCID 22258714, compound

HRID 1611114Notes

Reaction equation

HRID 1611114 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15](=[O:18])[CH2:16]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[FH:42].[F-]>C1COCC1.CCOCC>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15](=[O:18])[CH2:16][F:42])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 10891295Tetrabutylammonium bifluorideHCID 125418501-[2-(Benzyloxy)phenyl]-2-bromoethan-1-one

Product 1

HCID 22258714HCID 22258714, compoundYield 33.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[2-(benzyloxy)phenyl]-2-bromoethanone (2.59 g, 8.5 mmol) and pyridine (1.37 mL, 17 mmol) in THF was added tetrabutylammonium hydrogen difluoride (4.78 g, 17 mmol). The reaction mixture was stirred under reflux for 22 hrs. The mixture was diluted with ether (250 mL), then washed with 1N aqueous hydrochloric acid (100 mL) and brine (100 mL), successively. The organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (hexane/ethyl acetate, 4:1) to give 1-[2-(benzyloxy)phenyl]-2-fluoroethanone (688 mg, yield; 33%). [Starting Compound 1C]

Workup

  1. temperatureunder reflux for 22 hrs
  2. washwashed with 1N aqueous hydrochloric acid (100 mL) and brine (100 mL)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel (hexane/ethyl acetate, 4:1)

Sources & evidence

ORD record
ord-86d97c79c50d4e82b9ca442b53bee364
Source dataset
uspto-grants-2006_01
Patent number
US06984649B1

Reaction notes

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