Reaktion #441882

Reaktionsgleichung

potassium α-isopropyl-4-chlorophenylacetate

α-fluoro-3-phenoxy benzyl bromide

water

→

α-fluoro-3-phenoxybenzyl α-isopropyl-4-chlorophenylacetate

Ausbeute 41.4%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe aqueous solution was extracted with diethyl ether
2. 2
   ExtraktionThe ether extract
3. 3
   Waschenwas washed with aqueous sodium carbonate solution
4. 4
   Trocknenwas then dried over anhydrous sodium sulfate
5. 5
   SonstigeThe ether was removed by distillation under reduced pressure
6. 6
   Sonstigethe residue chromatographed over silica gel

Vorschrift

A mixture of potassium α-isopropyl-4-chlorophenylacetate (0.91 g) and α-fluoro-3-phenoxy benzyl bromide (1.06 g) in dimethylformamide (10 ml) was stirred at ambient temperature over a period of 2 hours. The reaction mixture was poured into water and the aqueous solution was extracted with diethyl ether. The ether extract was washed with aqueous sodium carbonate solution and was then dried over anhydrous sodium sulfate. The ether was removed by distillation under reduced pressure and the residue chromatographed over silica gel to give α-fluoro-3-phenoxybenzyl α-isopropyl-4-chlorophenylacetate (0.62 g; 37%) as a colourless oil. The product was characterised by pmr spectroscopy. Chemical shift δppm (solvent CDCl3): 0.69(3H,d,J=6 Hz, CH3); 1.05(3H,d of d, J=6 Hz and J=2 Hz, CH3); 2.34(1H, m, --CH(CH3)2); 3.29 (1H, d, J=10 Hz, CH); 7.22(1H, d of d, J=56 Hz and J=2 Hz, CHF) and c. 7.24(13H, m, aromatic protons).

Quelle