5-Chloro-salicylaldehyde → 5-Chloro-2-hydroxy-3-iodobenzaldehyde

HRID 841874Notes

Reaction equation

HRID 841874 reaction equation
[I:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:17]=[C:14]([CH:15]=[O:16])[C:13]([OH:18])=[CH:12][CH:11]=1>CN(C)C=O.C(OCC)(=O)C>[I:1][C:12]1[CH:11]=[C:10]([Cl:9])[CH:17]=[C:14]([CH:15]=[O:16])[C:13]=1[OH:18]

Participants

5

Reactant 2

HCID 124815-Chloro-salicylaldehydeHCID 120273N-Iodosuccinimide2×

Product 1

HCID 37725455-Chloro-2-hydroxy-3-iodobenzaldehydeYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Iodosuccinimide (144.0 g, 0.641 mole) was added to a solution of 5-chlorosalicylaldehyde (100 g, 0.638 mole) in dimethylformamide (400 mL). The reaction mixture was stirred for 2 days at room temperature. Additional N-iodosuccinimide (20.0 g) was added and stirring was continued for additional 2 days. The reaction mixture was diluted with ethyl acetate (1 L), washed with hydrochloric acid (300 mL, 0.1N), water (300 mL), sodium thiosulfate (5%, 300 mL), brine (300 mL), dried (MgSO4) and was concentrated to dryness to afford the desired aldehyde as a pale yellow solid (162 g, 90% yield).

Workup

  1. stirringstirring
  2. waitwas continued for additional 2 days
  3. washwashed with hydrochloric acid (300 mL, 0.1N), water (300 mL), sodium thiosulfate (5%, 300 mL), brine (300 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationwas concentrated to dryness

Sources & evidence

ORD record
ord-f1b426817a274718ad39cf29fea69bc9
Source dataset
uspto-grants-2002_04
Patent number
US06372719B1

Reaction notes

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