Sodium Bicarbonate → 1-(2,6-Difluoro-4-iodophenyl)ethan-1-one

HRID 561998Notes

Reaction equation

HRID 561998 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4]([F:9])[C:3]=1[CH:10]([OH:12])[CH3:11].C(=O)([O-])O.[Na+].Cl[O-].[Na+]>C(Cl)Cl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[Na+].O.CC1(C)N([O])C(C)(C)CCC1>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4]([F:9])[C:3]=1[C:10](=[O:12])[CH3:11]

Participants

8

Reactant 3

HCID 516892Sodium BicarbonateHCID 23665760Sodium HypochloriteHCID 670012991-(2,6-Difluoro-4-iodophenyl)ethanol

Product 1

HCID 670012941-(2,6-Difluoro-4-iodophenyl)ethan-1-oneYield 94.2%

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 2724126TempoCatalystHCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 1-(2,6-difluoro-4-iodo-phenyl)-ethanol (561 mg, 1.98 mmol) in methylene chloride (25 mL) cooled in an ice/water bath were added 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) (3 mg, 0.12 mmol), sodium hydrogen carbonate (75 mg, 0.89 mmol) and tetrabutylammonium bromide (19 mg, 0.06 mmol). To this resulting mixture was added a 5% aqueous sodium hypochlorite solution in a dropwise manner until TLC indicated the reaction to be complete. The reaction mixture was diluted with methylene chloride (50 mL) and brine (100 mL) and the organic layer separated. The organic layer was dried over sodium sulfate, filtered through a pad of silica gel and concentrated in vacuo to give 1-(2,6-difluoro-4-iodo-phenyl)-ethanone (526 mg, 94%). HR-MS: calcd for C29H25F2IN4O4 [M+H+] 659.0962. Found 659.0962.

Workup

  1. customthe reaction
  2. customthe organic layer separated
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered through a pad of silica gel
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eda05d65cbe44137a9ae26adf67aed18
Source dataset
uspto-grants-2011_11
Patent number
US08063085B2

Reaction notes

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