Propanoic acid, 2-bromo-2-methyl-, ethyl ester → 2-Cyclohexylsulfanyl-2-methyl-propionic acid ethyl ester

To a solution of 2.5 g (21.5 mmol) of cyclohexyl thiol in ethanol (75 mL) were added 1.2 g (21.5 mmol) of KOH pellets, followed by 4.2 g (21.5 mmol) of ethyl α-bromoisobutyrate. The reaction was heated to reflux for 18 h and then cooled to room temperature. The solid (KBr) was separated by filtration and rinsed with ethanol (20 mL). The filtrate was concentrated under reduced pressure and the residue dissolved in DCM (50 mL). The organic layer was washed with water (2×20 mL). The aqueous washes were back-extracted with DCM (10 mL). The combined organics were washed with brine, dried over Na2SO4. Filtration and concentration under reduced pressure afforded 4.15 g of 2-cyclohexylsulfanyl-2-methyl-propionic acid ethyl ester.

1. temperatureThe reaction was heated
2. temperatureto reflux for 18 h
3. customThe solid (KBr) was separated by filtration
4. washrinsed with ethanol (20 mL)
5. concentrationThe filtrate was concentrated under reduced pressure
6. dissolutionthe residue dissolved in DCM (50 mL)
7. washThe organic layer was washed with water (2×20 mL)
8. extractionThe aqueous washes were back-extracted with DCM (10 mL)
9. washThe combined organics were washed with brine
10. dry with materialdried over Na2SO4
11. filtrationFiltration and concentration under reduced pressure

ORD record

ord-ca0b459394a94bc4878387108c6e8091

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07928123B2