Ethyl Acetate → 4-Bromo-2-chlorobenzaldehyde

HRID 219171

Reaktionsgleichung

Reaktionsgleichung von HRID 219171
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([Cl:10])[CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CCOC(C)=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[C:4]([Cl:10])[CH:3]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 159087TriacetoxyperiodinaneHCID 43805739(4-Bromo-2-chlorophenyl)methanol

Produkt 1

HCID 141091094-Bromo-2-chlorobenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirring solution of (4-bromo-2-chlorophenyl)methanol (4.5 g, 20 mmol) in DCM (50 mL) was added Dess-Martin periodinane (9.3 g) at 23° C. Reaction refluxed after addition. After 20 min, TLC (1:4 EtOAc/Hex) suggests full conversion of alcohol. Suspension then washed with 5% NaHCO3 (100 mL plus 15 g dry NaHCO3). Organic dried over MgSO4, concentrated onto dry silica (15 g), then purified on silica (120 g) eluting with 0>10% EtOAc/hex. 4-bromo-2-chlorobenzaldehyde isolated as a white solid.

Aufarbeitung

  1. customReaction
  2. temperaturerefluxed
  3. additionafter addition
  4. washSuspension then washed with 5% NaHCO3 (100 mL plus 15 g dry NaHCO3)
  5. dry with materialOrganic dried over MgSO4
  6. concentrationconcentrated onto dry silica (15 g)
  7. custompurified on silica (120 g)
  8. washeluting with 0>10% EtOAc/hex

Quellen und Nachweise

ORD-Eintrag
ord-52100ea894ab45d1803c130d97cacefb
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198448B2

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