1-Chloro-2-fluorobenzene → 1-Chloro-2-fluoro-3-(methylsulfanyl)benzene

A solution of 10 g (grams) (76 mmol (millimoles)) of 1-chloro-2-fluorobenzene in 75 mL (milliliters) of dry tetrahydrofuran (THF) was cooled with a dry ice/acetone bath and 34 mL (84 mmol) of 2.5M butyllithium was added dropwise under a nitrogen blanket over 45 min with stirring and cooling. The resulting solution was stirred for 2 hours at -78° C. A solution of 8.1 mL (91 mmol) of dimethyl disulfide in 10 mL of dry THF was added with stirring over a 30-min period keeping the temperature below -65° C. The mixture was allowed to warm to ambient temperature for 1 hour. It was then diluted with 75 mL of water. The resulting mixture was extracted with diethyl ether and the ether extract was dried over sodium sulfate and concentrated by evaporation under reduced pressure to obtain a yellow oil. This oil was purified by flash chromatography on 230-400 mesh silica gel eluting with a hexane/ethyl acetate mixture to obtain 9.0 g (69 percent of theory) of the title compound as a light yellow oil.

1. temperaturecooling
2. stirringThe resulting solution was stirred for 2 hours at -78° C
3. stirringwith stirring over a 30-min period
4. customthe temperature below -65° C
5. extractionThe resulting mixture was extracted with diethyl ether
6. extractionthe ether extract
7. dry with materialwas dried over sodium sulfate
8. concentrationconcentrated by evaporation under reduced pressure
9. customto obtain a yellow oil
10. customThis oil was purified by flash chromatography on 230-400 mesh silica gel eluting with a hexane/ethyl acetate mixture

ORD record

ord-b0ee5de67ce845d08ab6f2eb1edd7594

Source dataset

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06140271