Reaktion #2012726

Reaktionsgleichung

acetic acid

K2CO3

2-mercapto-nicotinic acid

1-(3-bromopropyl)-4-fluorobenzene

→

2-(3-(4-fluoro-phenyl)propylthio)nicotinic acid

Ausbeute 47.0%

Lösungsmittel

DMF

water

EA

EA hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas carried out for a further 72 h at RT
3. 3
   SonstigeThe organic phase was separated off
4. 4
   Waschenwashed with water
5. 5
   Trocknendried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated in vacuo

Vorschrift

4.9 g (35.8 mmol) of K2CO3 were added to a solution of 2.5 g (16.3 mmol) of 2-mercapto-nicotinic acid in DMF (40 ml), and the mixture was stirred for 30 min at RT. 3.5 g (16.3 mmol) of 1-(3-bromopropyl)-4-fluorobenzene were then added and stirring was carried out for a further 72 h at RT. The mixture was then diluted with water and EA and adjusted to pH 5-6 with 5M acetic acid. The organic phase was separated off, washed with water, dried over MgSO4, filtered and concentrated in vacuo. CC (EA/hexane 1:2→5:1) of the residue yielded 2.2 g (7.6 mmol, 47%) of 2-(3-(4-fluoro-phenyl)propylthio)nicotinic acid.

Quelle