Triacetoxyperiodinane → 4-Bromo-2-methylbenzaldehyde

HRID 1499260Notes

Reaction equation

HRID 1499260 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([CH3:10])[CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[C:4]([CH3:10])[CH:3]=1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 22280088(4-Bromo-2-methylphenyl)methanol

Product 1

HCID 135551504-Bromo-2-methylbenzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To the solution of (4-bromo-2-methylphenyl)methanol (1.8 g, 8.1 mmol) in CH2Cl2 (20 mL) was added Dess-Martin Periodinane (5.1 g, 12.1 mmol) at 0° C. The mixture was stirred at RT for 1 h, then diluted with water, and the solid was removed by filtration. The filtrate was extracted with CH2Cl2. The combined organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. Purification by normal phase silica gel column provided 4-bromo-2-methylbenzaldehyde as a yellow oil.

Workup

  1. customthe solid was removed by filtration
  2. extractionThe filtrate was extracted with CH2Cl2
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification by normal phase silica gel column

Sources & evidence

ORD record
ord-0123451af57f4b92a44e1f9a4dedb9fc
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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