4-Bromo-3-methylbenzaldehyde → 1-(4-Bromo-3-methylphenyl)ethanol

HRID 1500958

Reaktionsgleichung

Reaktionsgleichung von HRID 1500958
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:10].[CH3:11][Mg]Br>O1CCCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([OH:7])[CH3:11])=[CH:4][C:3]=1[CH3:10]

Komponenten

4

Edukt 2

HCID 109215214-Bromo-3-methylbenzaldehydeHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 790169431-(4-Bromo-3-methylphenyl)ethanolAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 4-bromo-3-methylbenzaldehyde (4 g, 20 mmol) in dry tetrahydrofuran (40 mL) was cooled to 0° C. under nitrogen atmosphere, and then methyl magnesium bromide (20 mL, 1N in tetrahydrofuran) was added dropwise. The ice bath was removed, and the mixture was stirred for 2 hours. Ammonium chloride aqueous (40 mL) was added and the mixture was extracted with dichloromethane (20 mL*3). The organic phase was dried by sodium sulphate, filtered and concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1) to give 1-(4-bromo-3-methylphenyl)ethanol as a colorless oil (4.0 g, 93%).

Aufarbeitung

  1. customThe ice bath was removed
  2. additionAmmonium chloride aqueous (40 mL) was added
  3. extractionthe mixture was extracted with dichloromethane (20 mL*3)
  4. dry with materialThe organic phase was dried by sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a residue
  8. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-3c09379f6f814c23a4c8fae66de6dac7
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206128B2

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