Triacetoxyperiodinane → 3-Bromo-2-methylbenzaldehyde

HRID 661855Notes

Reaction equation

HRID 661855 reaction equation
[Br:1][C:2]1[C:3]([CH3:10])=[C:4]([CH2:8][OH:9])[CH:5]=[CH:6][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>C1COCC1.CCOCC>[Br:1][C:2]1[C:3]([CH3:10])=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH:8]=[O:9]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 10035697(3-Bromo-2-methylphenyl)methanol

Product 1

HCID 104427433-Bromo-2-methylbenzaldehydeYield 70%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Step 1 A mixture of (3-bromo-2-methylphenyl)methanol (prepared according to the procedures reported in US Pat. Appl. 2006/0173183, 500 mg, 2.49 mmol) in THF (20 mL) was stirred at rt and treated with 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (Dess-Martin periodinane, 1.58 g, 3.73 mmol). After 2 h, the mixture was diluted with ether (ca. 100 mL) and washed with 5% aqueous sodium bisulfite, NaHCO3 (aq) and brine, dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from hexane to 55:45 hexane-EtOAc) to provide 3-bromo-2-methylbenzaldehyde as a colorless oil (343 mg, 70%). 1H NMR (400 MHz, chloroform-d) δ 10.26 (1H, s), 7.78 (2H, ddd, J=9.7, 8.0, 1.2 Hz), 7.20-7.27 (1H, m), 2.75 (3H, s).

Workup

  1. customprepared
  2. washwashed with 5% aqueous sodium bisulfite, NaHCO3 (aq) and brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (
  6. washeluting with a gradient from hexane to 55:45 hexane-EtOAc)

Sources & evidence

ORD record
ord-f5142bae7e2b47259f899368377ef4cb
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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