Dichloromethane → 2-Chloro-5-iodobenzaldehyde

HRID 602058Notes

Reaction equation

HRID 602058 reaction equation
C(Cl)Cl.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:6]=1[CH2:12][OH:13].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>CCOCC>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:6]=1[CH:12]=[O:13]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 671539432-Chloro-5-iodobenzyl alcoholHCID 178418287HCID 178418287, compound

Product 1

HCID 221152692-Chloro-5-iodobenzaldehydeYield 67%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A methylene chloride solution (99 mL) of (2-chloro-5-iodophenyl)methanol (9.01 g, 33.5 mmol) and PCC (8.67 g, 40.2 mmol) were combined and stirred at rt. After 16 h, Et2O was added and the solution stirred for 30 minutes. The solution was then filtered and the organic layer was washed with H2O (2×), NaHCO3 (3×), and brine. The organic layer was dried (Na2SO4), concentrated, and purified by Biotage chromatography (0%-20% EtOAc/hexanes) to afford 5.94 g of product (67%). 1H NMR (400 MHz, chloroform-d) δ ppm 10.38 (s, 1 H) 8.22 (d, J=2.02 Hz, 1 H) 7.83 (dd, J=8.46, 2.15 Hz, 1 H) 7.21 (d, J=8.59 Hz, 1 H).

Workup

  1. stirringthe solution stirred for 30 minutes
  2. filtrationThe solution was then filtered
  3. washthe organic layer was washed with H2O (2×), NaHCO3 (3×), and brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified by Biotage chromatography (0%-20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-212cfaf3c2f640db8ebeb4e873cca89c
Source dataset
uspto-grants-2011_03
Patent number
US07902394B2

Reaction notes

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