Water → alpha-Fluoro-3-phenoxybenzyl alpha-isopropyl-4-chlorophenylacetate

Participants

Reaction Steps

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).

Provenance & Evidence