Reaktion #531902

Reaktionsgleichung

4-fluorophenylacetic acid

3,4-difluorobenzaldehyde

Ac2O

diisopropylethylamine

HCl

→

product

Ausbeute 121.6%

3-(3,4-difluorophenyl)-2-(4-fluorophenyl)acrylic acid

Ausbeute 121.6%

Lösungsmittel

DCM MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added to the reaction mixture
2. 2
   Sonstigethe precipitate formed
3. 3
   Filtrationwas filtered
4. 4
   workup.DISSOLUTIONdissolved in CH2Cl2 (100 mL)
5. 5
   WaschenThe organic layer was washed with 10% aqueous NaOH (3×50 mL)
6. 6
   SonstigeThe precipitate formed
7. 7
   Filtrationwas filtered
8. 8
   Waschenwashed with water (100 mL)
9. 9
   Sonstigedried

Vorschrift

A mixture of 4-fluorophenylacetic acid (2 g, 13 mmol), 3,4-difluorobenzaldehyde (2.5 g, 13 mmol), Ac2O (10 mL) and diisopropylethylamine (2.9 mL) was stirred at room temperature for 12 hours. Upon completion, as monitored by TLC using DCM:MeOH (9:1) as the eluent, 10 mL 10% aqueous HCl was added to the reaction mixture, the precipitate formed was filtered and dissolved in CH2Cl2 (100 mL). The organic layer was washed with 10% aqueous NaOH (3×50 mL) and the basic aqueous solution was acidified with 10% aqueous HCl to pH 3. The precipitate formed was filtered, washed with water (100 mL) and dried to get the product (4.4 g, 41.5% yield).

Quelle