Hydrochloric Acid → 5-Formyl-2-propoxybenzonitrile

HRID 717722

Reaktionsgleichung

Reaktionsgleichung von HRID 717722
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][CH3:13])[CH:5]=[O:6].[CH3:14][N:15](C=O)C.Cl>CCOC(C)=O>[CH:5]([C:4]1[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH2:12][CH3:13])=[C:2]([CH:3]=1)[C:14]#[N:15])=[O:6]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 47700413-Bromo-4-propoxybenzaldehyde

Produkt 1

HCID 866606335-Formyl-2-propoxybenzonitrileAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-bromo-4-propoxybenzaldehyde (0.6 g, 2.47 mmol) in anhydrous DMF (5 ml) CuCN (0.67 g; 7.4 mmol) was added and the mixture was stirred for 4 h at reflux. After cooling to room temperature, the mixture was treated with EtOAc (50 ml) and 1M HCl (10 ml) and stirred for 15 min. The organic layer was separated, dried over MgSO4 and filtered. The filtrate was evaporated to dryness to give 5-formyl-2-propoxybenzonitrile (0.41 g; 88%), as yellow oil 1H NMR (CDCl3) 9.87 (s, 1H); 8.07 (d, 1H, J=1.95 Hz); 8.03 (dd, 1H, J=8.67, 2.1 Hz); 7.06 (d, 1H, J=8.7 Hz); 4.13 (t, 2H, J=6.45 Hz); 1.97-1.85 (m, 2H); 1.1 (t, 3H, J=7.35 Hz). The above benzaldehyde was oxidised via a similar procedure as described in Example 47 Step A, to give the title compound (0.29 g; 68%), as white solid. 1H NMR (CDCl3) 8.3 (d, 1H, J=1.71 Hz); 8.23 (dd, 1H, J=8.88, 2.1 Hz); 7.00 (d, 1H, J=7.62 Hz); 4.12 (t, 2H, J=6.48 Hz); 1.97-1.85 (m, 2H); 1.09 (t, 3H, J=7.38 Hz).

Aufarbeitung

  1. temperatureat reflux
  2. stirringstirred for 15 min
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-df43d3f87291472094bb30c5c4ac89a8
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193716B2

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