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

HRID 841873Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 841873
[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]

Komponenten

6

Edukt 3

HCID 4875Potassium IodideHCID 31388TosylchloramideHCID 728635-Bromosalicylaldehyde

Produkt 1

HCID 27166955-Bromo-2-hydroxy-3-iodobenzaldehydeAusbeute 79,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-2c7bbfe386384bdc88310e70810ebc6e
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06372719B1

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