Triacetoxyperiodinane → (2-Bromo-5-fluorophenyl)(phenyl)methanone

HRID 469549Notes

Reaction equation

HRID 469549 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Br:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[CH:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[OH:32]>C(Cl)Cl.CCOC(C)=O>[Br:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[C:31]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)=[O:32]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 61100031(2-Bromo-5-fluorophenyl)(phenyl)methanol

Product 1

HCID 242877(2-Bromo-5-fluorophenyl)(phenyl)methanoneYield 92.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Dess-Martin periodinane (0.931 g, 2.20 mmol) and the product of example 35A (0.561 g, 2.00 mmol) was stirred in CH2Cl2 (10 mL) for 1 hour, diluted with EtOAc, washed with saturated aqueous NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated. The residue was chromatographed on SiO2 (eluted with 4% Et2O/hexanes) to give 515.6 mg of the title compound as a clear gum. 1H NMR (300 MHz, DMSO) δ 7.81 (dd, 1H), 7.69-7.76 (m, 3H), 7.54-7.61 (m, 2H), 7.50 (dd, 1H), 7.39 (ddd, 1H).

Workup

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was chromatographed on SiO2 (eluted with 4% Et2O/hexanes)

Sources & evidence

ORD record
ord-fe81e6f2c6074e6e827279c953a42978
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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