Water → 2-Fluoro-5-hydroxybenzaldehyde

HRID 734729

Reaktionsgleichung

Reaktionsgleichung von HRID 734729
B(Br)(Br)Br.[F:5][C:6]1[CH:13]=[CH:12][C:11]([O:14]C)=[CH:10][C:7]=1[CH:8]=[O:9].O>C(Cl)Cl>[F:5][C:6]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:7]=1[CH:8]=[O:9]

Komponenten

5

Edukt 3

HCID 962WaterHCID 25134Boron tribromideHCID 27348722-Fluoro-5-methoxybenzaldehyde

Produkt 1

HCID 5872472-Fluoro-5-hydroxybenzaldehydeAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

BBr3 (4 mL, 4 mmol, 1.0 M in heptane) was added dropwise to a solution of 2-fluoro-5-(methyloxy)benzaldehyde in CH2Cl2 at −78° C. The reaction mixture was stirred at −78° C. for 1 hour, slowly warmed to 0° C. and stirred for 2 hours. The reaction mixture was poured into water, extracted with EtOAc (3×10 mL). The extracts were combined, washed with water, brine, and dried (Na2SO4). The solvent was evaporated, and the residue was purified on silica gel, using 0-20% EtOAc-Hexane to give the desired product (142 mg, 25%) as a white solid. MS m/z 141 [M+H]+

Aufarbeitung

  1. temperatureslowly warmed to 0° C.
  2. stirringstirred for 2 hours
  3. extractionextracted with EtOAc (3×10 mL)
  4. washwashed with water, brine
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was evaporated
  7. customthe residue was purified on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-ff0e585d93b041cd836cc2257033261f
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592357B2

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