4-Bromobenzaldehyde → 1-(4-Bromophenyl)hexan-1-ol

HRID 1161753

Reaktionsgleichung

Reaktionsgleichung von HRID 1161753
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH3:5].[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=1>C1COCC1>[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]([OH:14])[CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:11][CH:10]=1

Komponenten

4

Edukt 2

HCID 707414-BromobenzaldehydeHCID 178445865HCID 178445865, Verbindung

Produkt 1

HCID 126030861-(4-Bromophenyl)hexan-1-olAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

n-Pentyl magnesium bromide (2.0 M in THF, 27 mL, 54 mmol) was added to a solution of 4-bromobenzaldehyde (5.0 g, 27 mmol) in THF (20 mL) at 0° C. under nitrogen. After 1 h, the reaction was quenched with 3 N HCl and extracted with Et2O (3×120 mL). Combined extracts were washed with brine (100 mL), dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel (5% EtOAc/Hex) afforded 5.1 g (74%) of 1-(4-bromophenyl)-hexan-1-ol.

Aufarbeitung

  1. customthe reaction was quenched with 3 N HCl
  2. extractionextracted with Et2O (3×120 mL)
  3. washCombined extracts were washed with brine (100 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by flash column chromatography on silica gel (5% EtOAc/Hex)

Quellen und Nachweise

ORD-Eintrag
ord-9e2c49d5a3db47a8b98bd458f28c93d6
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820661B2

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