Ethyl Bromide → 3-Ethoxy-6-fluoro-2-hydroxy-benzaldehyde

HRID 2367979Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2367979
[F:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([OH:10])[C:5]([OH:11])=[CH:4][CH:3]=1.[CH2:12](Br)[CH3:13]>CS(C)=O.O>[CH2:12]([O:11][C:5]1[C:6]([OH:10])=[C:7]([C:2]([F:1])=[CH:3][CH:4]=1)[CH:8]=[O:9])[CH3:13]

Komponenten

5

Edukt 2

HCID 6332Ethyl BromideHCID 866647326-Fluoro-2,3-dihydroxybenzaldehyde

Produkt 1

HCID 866647343-Ethoxy-6-fluoro-2-hydroxy-benzaldehydeAusbeute 89,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 6-fluoro-2,3-dihydroxy-benzaldehyde (1.00 g, 6.40 mmol) in dry DMSO (10 mL) was added NaOBut (1.23 g, 12.81 mmol) and ethyl bromide (0.77 g, 7.04 mmol) under N2 and stirred at RT for 18 h. The resultant mixture was diluted with water, acidified to pH ˜6 with 2N.HCl and extracted with EtOAc (4×25 mL). Combined organic layers were washed with water and brine and dried over MgSO4. Filtration and removal of the solvent under reduced pressure provided 1.05 g (5.70 mmol, 89%) of the title compound as yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 10.24 (s, 1H), 7.04 (dd, J=8.8, 5.3 Hz, 1H), 6.61-6.50 (m, 1H), 4.09 (q, J=7.0 Hz, 3H), 1.46 (t, J=7.0 Hz, 3H); 19F NMR (376 MHz, CHLOROFORM-d) δ ppm −132.19-−132.15 (m, 1F).

Aufarbeitung

  1. extractionHCl and extracted with EtOAc (4×25 mL)
  2. washCombined organic layers were washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationFiltration and removal of the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7aefcc4fed0e411585ccf84af0939f53
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703742B2

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