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

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).

1. extractionthe aqueous solution was extracted with diethyl ether
2. extractionThe ether extract
3. washwas washed with aqueous sodium carbonate solution
4. dry with materialwas then dried over anhydrous sodium sulfate
5. customThe ether was removed by distillation under reduced pressure
6. customthe residue chromatographed over silica gel

ORD record

ord-3c6f068a9ec345f58cffee4036939934

Source dataset

uspto-grants-1983_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04376784