Ethyl Acetate → (2-Bromo-5-ethoxy-4-methylphenyl)methanol

HRID 402765Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 402765
[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([O:12][CH2:13][CH3:14])=[CH:7][C:3]=1[C:4]([O-])=[O:5].CC(C[AlH]CC(C)C)C.CCOC(C)=O>CCOCC>[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([O:12][CH2:13][CH3:14])=[CH:7][C:3]=1[CH2:4][OH:5]

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 14487Diisobutylaluminum hydrideHCID 866768062-Bromo-5-ethoxy-4-methylbenzoate

Produkt 1

HCID 66764839(2-Bromo-5-ethoxy-4-methylphenyl)methanolAusbeute 100,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2-bromo-5-ethoxy-4-methylbenzoate (660 mg, 2.23 mmol) in ether (20 mL) at 0° C. was added DIBAL (5.75 mL, 5.75 mmol, 1 M in toluene). The reaction was stirred at 0° C. for 10 minutes. EtOAc (20 mL) and wet silica gel (˜50 g silica gel and 3 mL of water) were added portion wise at 0° C. The resulting slurry was stirred for ˜15 minutes and was filtered, washed with EtOAc (20 mL). The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was purified on a silica gel column eluting with EtOAc/hexanes (20/80) to give the title intermediate (550 mg) as colorless liquid.

Aufarbeitung

  1. stirringThe resulting slurry was stirred for ˜15 minutes
  2. filtrationwas filtered
  3. washwashed with EtOAc (20 mL)
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on a silica gel column
  8. washeluting with EtOAc/hexanes (20/80)

Quellen und Nachweise

ORD-Eintrag
ord-13f7f37a386f4f338cfb418d935bb65f
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08742110B2

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