Réaction #972682

Équation de réaction

2-bromo-hexanoic acid methyl ester

4-fluoro-3-methylaniline

K2CO3

→

title compound

Rendement 45.0%

2-(4-Fluoro-3-methyl-phenylamino)-hexanoic acid methyl ester

Rendement 45.0%

Solvants

DMF

water

Conditions de réaction

Traitement

1. 1
   Extractionextracted with dichloromethane (60 mL×3)
2. 2
   SéchageThe organic extracts were combined dried over anhydrous Na2SO4
3. 3
   Autrethe solvent removed under reduced pressure
4. 4
   LavageFlash chromatography (silica gel) eluting with 0-20% ethyl acetate/hexanes

Mode opératoire

To a solution of 2-bromo-hexanoic acid methyl ester (0.500 g, 2.404 mmol) and 4-fluoro-3-methylaniline (0.301 g, 2.404 mmol) in 15 mL of DMF, was added K2CO3 (1.661 g, 12.020 mmol). After stirring at room temperature under N2 for 88 h, the reaction mixture was diluted with 60 mL of water and extracted with dichloromethane (60 mL×3). The organic extracts were combined dried over anhydrous Na2SO4 and the solvent removed under reduced pressure. Flash chromatography (silica gel) eluting with 0-20% ethyl acetate/hexanes afforded the title compound as brown oil (0.273 g, 45% yield). LC-MS: tR=9.9 min; m/z 254 (M+H)+.

Source