Dimethylformamide → 3-Chloro-5-methoxybenzaldehyde

HRID 505009Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 505009
Cl[C:2]1[CH:3]=[C:4]([O:9][CH3:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Mg].CN(C)[CH:14]=[O:15].CCOC(C)=O>C1COCC1.BrCCBr>[Cl:8][C:6]1[CH:7]=[C:2]([CH:3]=[C:4]([O:9][CH3:10])[CH:5]=1)[CH:14]=[O:15]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 365883,5-DichloroanisoleHCID 5462224Magnesium

Produkt 1

HCID 219046333-Chloro-5-methoxybenzaldehydeAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 78391,2-DibromoethaneKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3,5-Dichloroanisole (74.0 g, 419 mmol) in THF (200 mL) was added dropwise to magnesium metal (14.2 g, 585 mmol, pre-washed with 0.5 N HCl) in THF (100 mL) at 25° C. After the addition, 1,2-dibromoethane (3.9 g, 20.8 mmol) was added dropwise. The resultant dark brown mixture was heated at reflux for 3 h. The mixture was cooled to 0° C., and N,N-dimethylformamide (60 mL) was added in one portion. The mixture was partitioned with diethyl ether (3×400 mL) and 6N HCl (500 mL). The combined organic extracts were washed with brine (300 mL), dried (Na2SO4), filtered and concentrated in vacuo to give an oil. Flash chromatography (2×) on silica gel eluting with Hex:EtOAc (4:1) afforded the sub-title compound (38.9 g, 54%) as a yellow oil.

Aufarbeitung

  1. additionwas added dropwise
  2. temperatureThe resultant dark brown mixture was heated
  3. temperatureat reflux for 3 h
  4. customThe mixture was partitioned with diethyl ether (3×400 mL) and 6N HCl (500 mL)
  5. washThe combined organic extracts were washed with brine (300 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give an oil

Quellen und Nachweise

ORD-Eintrag
ord-cc3046cd0f33442e9fd5e9760d1ffc81
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781424B2

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