5-Chloro-salicylaldehyde → 277312-89-7

HRID 983786Notes

Reaction equation

HRID 983786 reaction equation
[H][H].[Cl:3][C:4]1[CH:5]=[CH:6][C:7](O)=[C:8]([CH:11]=1)[CH:9]=[O:10].[I:13]N1C(=O)CCC1=O>C(O)(=O)C.C(OCC)(=O)C>[Cl:3][C:4]1[CH:5]=[C:6]([I:13])[CH:7]=[C:8]([CH:11]=1)[CH:9]=[O:10]

Participants

6

Reactant 3

HCID 124815-Chloro-salicylaldehydeHCID 120273N-Iodosuccinimide2×HCID 178418361HCID 178418361, compound

Product 1

HCID 22556934277312-89-7

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

Scheme VI depicts a method for preparing aldehyde 15. For example, a mixture of an aldehyde of formula 14 wherein R3 and R5 are hydrogen, i.e., 5-chloro,2-hydroxy benzaldehyde (0.10 g, 0.64 mmol) and N-iodosuccinimide (0.16 g, 0.71 mmol) in acetic acid (2 mL) was heated to 95° C. for 2 h. Another portion of N-iodosuccinimide (0.020 g, 0.09 mmol) was added and heating was continued for 1 h. The mixture was diluted with ethyl acetate, washed in succession with 5% aqueous Na2S2O3, saturated NaCl, and dried (Na2SO4). The solvent was removed under reduced pressure, and 5-chloro-3-iodo-benzaldehyde was obtained as a yellow crystalline solid (0.17 g, 94%)

Workup

  1. temperatureheating
  2. washwashed in succession with 5% aqueous Na2S2O3, saturated NaCl
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-09d5463606094e59932e6931d47b8cd8
Source dataset
uspto-grants-2005_03
Patent number
US06867200B1

Reaction notes

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