Triacetoxyperiodinane → 3',5'-Difluoroacetophenone

HRID 1499588Notes

Reaction equation

HRID 1499588 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[F:23][C:24]1[CH:25]=[C:26]([CH:31]([OH:33])[CH3:32])[CH:27]=[C:28]([F:30])[CH:29]=1>C(Cl)Cl>[F:23][C:24]1[CH:25]=[C:26]([C:31](=[O:33])[CH3:32])[CH:27]=[C:28]([F:30])[CH:29]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 27823261-(3,5-Difluorophenyl)ethan-1-ol

Product 1

HCID 5185963',5'-DifluoroacetophenoneYield 69.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (9.66 g, 22.8 mmol) was added portionwise to a solution of 1-(3,5-difluorophenyl)ethanol (3.00 g, 19.0 mmol) in DCM (40 mL) cooled in an ice bath. The mixture was stirred at room temperature for 2 h, then concentrated under reduced pressure. The residue was purified by purified by column chromatography on silica gel using CombiFlash® apparatus eluting with EtOAc/hexanes (0-40%). The purification gave 2.06 g (69.6%) of the sub-title compound as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 7.45 (m, 2H), 7.01 (m, 1H), 2.59 (s, 3H) ppm.

Workup

  1. temperaturecooled in an ice bath
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified
  4. customby purified by column chromatography on silica gel using CombiFlash® apparatus
  5. washeluting with EtOAc/hexanes (0-40%)
  6. customThe purification

Sources & evidence

ORD record
ord-3e1b728b6566477fbd3b393128e91738
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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