Triacetoxyperiodinane → 4-(4-Bromo-3,5-dimethylphenyl)butan-2-one

HRID 237536Notes

Reaction equation

HRID 237536 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH2:9][CH2:10][CH:11]([OH:13])[CH3:12])=[CH:4][C:3]=1[CH3:14].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH2:9][CH2:10][C:11](=[O:13])[CH3:12])=[CH:4][C:3]=1[CH3:14]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 866971984-(4-Bromo-3,5-dimethylphenyl)butan-2-ol

Product 1

HCID 866971994-(4-Bromo-3,5-dimethylphenyl)butan-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(4-bromo-3,5-dimethylphenyl)butan-2-ol (130 mg) in dichloromethane (8 mL) is added at 0° C. 1,1-dihydro-1,1,1-triacetoxy-1,2-benziodoxol-3(1H)-on (Dess-Martin periodinan, 1.4 mL of a 15% solution in dichloromethane). The mixture is stirred for 12 hours at room temperature. The solvents are evaporated in vacuo. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→70:30) to give the title compound. Yield: 100 mg; LC (method 8): tR=0.44 min; Mass spectrum (ESI+): m/z=255 [M+H]+.

Workup

  1. customThe solvents are evaporated in vacuo
  2. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→70:30)

Sources & evidence

ORD record
ord-7cc07d8fe73748e8af59e176ac5f9b66
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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