p-Chlorothiophenol → 6-(4-Chlorophenylsulfanyl)-hexanoic acid methyl ester

To a solution of 6-bromohexanoic acid methyl ester (2.1 g, 10 mmol), triethylamine (1.6 mL, 11 mmol) and tert-butylammonium iodide (200 mg, 0.54 mmol) in freshly distilled THF (30 mL) was added 4-chlorothiophenol (1.45 g, 10 mmol) under an atmosphere of argon. The mixture was stirred at reflux for 2 hours after which it was concentrated under reduced pressure. The oil was dissolved in ethyl acetate (100 mL) and then washed successively with saturated aqueous sodium hydrogen carbonate (50 mL), distilled water (50 mL) and brine (50 mL). The organic layer was then dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give an yellow oil that was purified by flash chromatography (1:9 diethyl ether:40-60° C. petroleum ether). The title compound was obtained as a colourless oil (2.5 g, 93%).

1. temperatureat reflux for 2 hours after which it
2. concentrationwas concentrated under reduced pressure
3. dissolutionThe oil was dissolved in ethyl acetate (100 mL)
4. washwashed successively with saturated aqueous sodium hydrogen carbonate (50 mL)
5. distillationdistilled water (50 mL) and brine (50 mL)
6. dry with materialThe organic layer was then dried over anhydrous MgSO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customto give an yellow oil that
10. customwas purified by flash chromatography (1:9 diethyl ether:40-60° C. petroleum ether)

ORD record

ord-d207af902e3c4338b68da53077d44016

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07683185B2