Iodine → HCID 22259699, compound

HRID 1508475Notes

Reaction equation

HRID 1508475 reaction equation
[I:1]I.I([O-])(=O)(=O)=O.[Na+].[CH2:9]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1)[CH3:10]>OS(O)(=O)=O>[CH2:9]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][C:12]=1[I:1])[CH3:10]

Participants

5

Reactant 3

HCID 807IodineHCID 208614-EthylbenzaldehydeHCID 23667635Sodium periodate

Product 1

HCID 22259699HCID 22259699, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
27.5 °C

Procedure

Iodine (0.245 mL, 4.73 mmol) and sodium metaperiodate (0.340 g, 1.59 mmol) were added slowly portionwise successively to stirred 95% H2SO4 (30.0 mL) at 25° C. and the mixture was stirred for 30 min to afford a dark brown iodinating solution. The iodinating solution was added dropwise to a stirred suspension of 4-ethylbenzaldehyde (1.34 g, 10 mmol) in 95% H2SO4 (10.0 mL) over 45 min while maintaining the temperature at 25-30° C. Stirring was continued for a further 15 min and the reaction was quenched by slowly pouring into stirred ice-water (300 mL). The precipitate was collected by filtration, washed with water and dried under vacuum to afford 4-ethyl-3-iodobenzaldehyde, as a colorless solid. 1H NMR (600 MHz, CDCl3): δ 9.87 (s, 1H); 8.28 (d, J=1.7 Hz, 1H); 7.77 (dd, J=7.8, 1.6 Hz, 1H); 7.36 (d, J=7.8 Hz, 1H); 2.78 (q, J=7.6 Hz, 2H); 1.23 (t, J=7.6 Hz, 4H).

Workup

  1. customto afford a dark brown iodinating solution
  2. stirringStirring
  3. waitwas continued for a further 15 min
  4. customthe reaction was quenched
  5. additionby slowly pouring
  6. stirringinto stirred ice-water (300 mL)
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with water
  9. customdried under vacuum

Sources & evidence

ORD record
ord-da3a9914cb8c4d56815999396af5113b
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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