Propanoic acid, 2-bromo-2-methyl-, ethyl ester → HCID 59703980, compound

To a solution of 5 g (48.7 mmol) of cyclopentyl thiol in ethanol (50 mL) are added 2.7 g (48.75 mmol) of KOH pellets, followed by 9.5 g (48.7 mmol) of ethyl α-bromoisobutyrate. The reaction is heated to reflux for 2 h and then cooled to room temperature. The solid (KBr) is separated by filtration and rinsed with ethanol (20 mL). The filtrate is concentrated under reduced pressure and the residue dissolved in DCM (50 mL). The organic layer is washed with saturated aqueous NaHCO3 solution (50 mL). The aqueous washes are back-extracted with DCM (10 mL). The combined organics are washed with brine, dried over Na2SO4. Filtration and concentration under reduced pressure affords 8.1 g of 2-cyclopentylsulfanyl-2-methyl-propionic acid ethyl ester. Yield: 77%, ES-MS: m/z 217 [M+H]

1. temperatureThe reaction is heated
2. temperatureto reflux for 2 h
3. customThe solid (KBr) is separated by filtration
4. washrinsed with ethanol (20 mL)
5. concentrationThe filtrate is concentrated under reduced pressure
6. dissolutionthe residue dissolved in DCM (50 mL)
7. washThe organic layer is washed with saturated aqueous NaHCO3 solution (50 mL)
8. extractionThe aqueous washes are back-extracted with DCM (10 mL)
9. washThe combined organics are washed with brine
10. dry with materialdried over Na2SO4
11. filtrationFiltration and concentration under reduced pressure

ORD record

ord-4c4a48e54f0e4184916249c015896ede

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08048899B2