4-Bromobenzaldehyde → p-Bromobenzhydryl alcohol

HRID 509177

Reaktionsgleichung

Reaktionsgleichung von HRID 509177
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10]1([Mg]Br)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1COCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[OH:7])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 707414-BromobenzaldehydeHCID 178418255HCID 178418255, Verbindung

Produkt 1

HCID 98221p-Bromobenzhydryl alcoholAusbeute 65,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of p-bromobenzaldehyde 10 (4 g, 21.6 mmol) in THF (20 mL) was added phenyl magnesium bromide (22.7 mL, 22.7 mmol) and the reaction mixture was stirred at room temperature for 30 minutes, quenched with water and partially concentrated under vacuum. The crude material was dissolved in ethyl acetate and washed with water. The organic layer was separated, dried over Na2SO4, filtered and concentrated. The residue was purified via prep-HPLC (ISCO) in silica gel column with a gradient of ethyl acetate (5-45%) in hexanes to afford title compound 11 as a colorless oil (3.7 g, 65%). 1H NMR (DMSO-d6) δ (ppm): 7.49-7.45 (m, 2H), 7.36-7.17 (m, 7H), 5.98 (d, J=4.1 Hz, 1H), 5.68 (d, J=3.9 Hz, 1H).

Aufarbeitung

  1. customquenched with water
  2. concentrationpartially concentrated under vacuum
  3. dissolutionThe crude material was dissolved in ethyl acetate
  4. washwashed with water
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified via prep-HPLC (ISCO) in silica gel column with a gradient of ethyl acetate (5-45%) in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-7bfae734ebab4c12836f611a56949d96
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096565B2

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