Potassium Iodide → 5-Bromo-2-hydroxy-3-iodobenzaldehyde

HRID 849471Notes

Reaction equation

HRID 849471 reaction equation
[Br:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.[I-:11].[K+].CC1C=CC(S(NCl)(=O)=O)=CC=1>C(#N)C.O>[I:11][C:4]1[CH:3]=[C:2]([Br:1])[CH:9]=[C:6]([CH:7]=[O:8])[C:5]=1[OH:10]

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 31388TosylchloramideHCID 728635-Bromosalicylaldehyde

Product 1

HCID 27166955-Bromo-2-hydroxy-3-iodobenzaldehydeYield 79.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5-bromosalicylaldehyde (20.0 g, 0.1 mole) and potassium iodide (17 g, 0.1 mole) in acetonitrile (150 mL) and water (50 mL) in a 500 mL round bottom flask with magnetic stirrer was added chloramine T (23 g, 0.1 mole). The mixture was allowed to react for one hour. The reaction mixture was partitioned between hydrochloric acid (10%, 200 mL) and ethyl acetate. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. To the residue was added hexanes and the reaction mixture heated to 50° C. for 15 minutes. The undissolved material was removed by filtration. The filtrate was concentrated in vacuo to leave canary yellow 3-iodo-5-bromosalicylaldehyde (26 g).

Workup

  1. customto react for one hour
  2. customThe reaction mixture was partitioned between hydrochloric acid (10%, 200 mL) and ethyl acetate
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. additionTo the residue was added hexanes
  7. customThe undissolved material was removed by filtration
  8. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5de3a466ec4d4110b2d253a848f45529
Source dataset
uspto-grants-2000_01
Patent number
US06013651

Reaction notes

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