(4'-Bromo-4-(dimethylamino)biphenyl-2-yl)methanol → 4'-Bromo-4-(dimethylamino)biphenyl-2-carbaldehyde

HRID 1043437Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1043437
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]([CH3:16])[CH3:15])=[CH:10][C:9]=2[CH2:17][OH:18])=[CH:4][CH:3]=1>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH:17]=[O:18])=[CH:10][C:11]([N:14]([CH3:15])[CH3:16])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Komponenten

3

Edukt 1

HCID 59266574(4'-Bromo-4-(dimethylamino)biphenyl-2-yl)methanol

Produkt 1

HCID 592665494'-Bromo-4-(dimethylamino)biphenyl-2-carbaldehydeAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

IBX (3.29 g, 11.76 mmol) was added to a solution of (4′-bromo-4-(dimethylamino)biphenyl-2-yl)methanol (1.8 g, 5.88 mmol) in dmso (50 mL) and stirred at 40° C. for 3 hours. The reaction was diluted with water and extracted with diethyl ether. The ether layer was dried over MgSO4, filtered and evaporated to give the crude material. The crude product was purified on the Biotage (5-20% EtOAc:Hex) to give 4′-bromo-4-(dimethylamino)biphenyl-2-carbaldehyde (1.25 g, 4.11 mmol, 70% yield) as a yellow solid. 1H NMR (500 MHz, CHLOROFORM-d) δ 2.95-3.13 (m, 6H) 7.01 (dd, J=8.55, 3.05 Hz, 1H) 7.22 (m, 2H) 7.28-7.33 (m, 2H) 7.57 (m, 2H) 9.96 (s, 1H).

Aufarbeitung

  1. extractionextracted with diethyl ether
  2. dry with materialThe ether layer was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customto give the crude material
  6. customThe crude product was purified on the Biotage (5-20% EtOAc:Hex)

Quellen und Nachweise

ORD-Eintrag
ord-4974b1aeb3d0461487574852b37b97d4
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563505B2

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