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

HRID 565795Notes

Reaction equation

HRID 565795 reaction equation
[Cl:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.[I:11]N1C(=O)CCC1=O>CN(C)C=O.C(OCC)(=O)C>[I:11][C:4]1[CH:3]=[C:2]([Cl:1])[CH:9]=[C:6]([CH:7]=[O:8])[C:5]=1[OH:10]

Participants

5

Reactant 2

HCID 124815-Chloro-salicylaldehydeHCID 120273N-Iodosuccinimide

Product 1

HCID 37725455-Chloro-2-hydroxy-3-iodobenzaldehydeYield 645.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-lodosuccinimide (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 the stirring was continued for an additional 2 days. The reaction mixture was diluted with ethyl acetate (1 L), washed with hydrochloric acid (300 mL, 0.1 N), water (300 mL), sodium thiosulfate (5%, 300 mL), brine (300 mL), dried (MgSO4) and was concentrated to dryness to afford the desired aldehyde (162 g, 90% yield) as a pale yellow solid.

Workup

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

Sources & evidence

ORD record
ord-8ef50a96309d4339a011924f82047323
Source dataset
uspto-grants-2001_01
Patent number
US06172256B2

Reaction notes

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