Triacetoxyperiodinane → 3-Bromo-5-iodobenzaldehyde

HRID 337645Notes

Reaction equation

HRID 337645 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][OH:10])[CH:5]=[C:6]([I:8])[CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl.CCOCC>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([I:8])[CH:7]=1)[CH:9]=[O:10]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 15467379(3-Bromo-5-iodophenyl)methanol

Product 1

HCID 219353253-Bromo-5-iodobenzaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of (3-bromo-5-iodophenyl)methanol from the previous step (1.0 eq.) and Dess-Martin periodinane (1.18 eq.) was stirred at RT in dichloromethane (0.1 M) for 45 min. The reaction mixture was diluted with ether, filtered through a plug of SiO2, and the silica washed with a 3:1 (v/v) mixture of hexanes:EtOAc. The filtrate was concentrated in vacuo and passed again through a plug of SiO2, eluting with a 3:1 (v/v) mixture of hexanes:EtOAc to afford the title compound as a light yellow solid.

Workup

  1. filtrationfiltered through a plug of SiO2
  2. washthe silica washed with a 3:1 (v/v) mixture of hexanes
  3. concentrationThe filtrate was concentrated in vacuo
  4. washeluting with a 3:1 (v/v) mixture of hexanes

Sources & evidence

ORD record
ord-6897acc0ca1c4392a1990ff1b4fc9573
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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