Hydrochloric Acid → 4-(Benzyloxy)-3-bromobenzaldehyde

HRID 459160Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 459160
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[H-].[Na+].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl>CN(C)C=O>[CH2:13]([O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[Br:1])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 763083-Bromo-4-hydroxybenzaldehyde

Produkt 1

HCID 14943384-(Benzyloxy)-3-bromobenzaldehydeAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3-Bromo-4-hydroxy-benzaldehyde (1.9 g, 9.45 mmol) was added slowly, at 0° C., to a suspension of NaH 95% (290 mg, 11.34 nol) in dry N,N-dimethylformamide (45 mL). The mixture was stirred for 0.5 hours. Benzyl chloride (1.3 mL, 11.34 mmol) was added and the reaction stirred at room temperature overnight. 1N HCl (40 mL) was added and the layers separated. The aqueous layer was extracted with diethyl ether (5×50 mL) and the combined organic layers were dried (Na2SO4), filtered, and concentrated under vacuum. The residue was chromatographed (silica gel, hexanes/ethyl acetate 9:1) to produce 4-Benzyloxy-3-bromo-benzaldehyde as a white solid (2.47 g, 90%). 1H-NMR (CDCl3, 200.15 MHz): δ 9.82 (s, 1H), 8.09 (d, 1H, J=1.8), 7.76 (dd, 1H, J=8.4, 1.8), 7.47–7.32 (m, 5H), 7.02 (d, 1H, J=8.4), 5.24 (s, 2H.

Aufarbeitung

  1. stirringthe reaction stirred at room temperature overnight
  2. customthe layers separated
  3. extractionThe aqueous layer was extracted with diethyl ether (5×50 mL)
  4. dry with materialthe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was chromatographed (silica gel, hexanes/ethyl acetate 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-9e89b2dd88924b45b55e0974239ed655
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07192982B2

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