Sodium Carbonate → 1-(2,2-Dibromovinyl)-3-isobutylcyclobutane

To a solution of carbon tetrabromide (168 g) in methylene chloride (252 mL) was added dropwise a solution of triphenylphosphine (266 g) in methylene chloride (350 mL) at ice temperature. The mixture was stirred at ice temperature for 20 min. To the mixture was then added dropwise a solution of 3-isobutylcyclobutanecarbaldehyde in methylene chloride at ice temperature. The mixture was stirred at ice temperature for 20 min. After an addition of aqueous 10 w/v % sodium carbonate (1 L) dropwise to the mixture, the mixture was extracted with methylene chloride (200 mL×2). The combined organic layer was washed with water and brine, then dried over magnesium sulfate. The magnesium sulfate was filtered off and the filtrate was concentrated in vacuo. To the resultant residue were added hexane/chloroform=1/1 (750 mL), silica gel (750 mL) and hexane (900 mL). The mixture was filtered and the filtrate was concentrated in vacuo. To the resultant residue was added hexane (500 mL). The mixture was filtered and the filtrate was concentrated in vacuo. The resultant residue was purified by silica gel column chromatography (Eluent: hexane) to give the title compound (76.21 g).

1. stirringThe mixture was stirred at ice temperature for 20 min
2. extractionthe mixture was extracted with methylene chloride (200 mL×2)
3. washThe combined organic layer was washed with water and brine
4. dry with materialdried over magnesium sulfate
5. filtrationThe magnesium sulfate was filtered off
6. concentrationthe filtrate was concentrated in vacuo
7. additionTo the resultant residue were added hexane/chloroform=1/1 (750 mL), silica gel (750 mL) and hexane (900 mL)
8. filtrationThe mixture was filtered
9. concentrationthe filtrate was concentrated in vacuo
10. additionTo the resultant residue was added hexane (500 mL)
11. filtrationThe mixture was filtered
12. concentrationthe filtrate was concentrated in vacuo
13. customThe resultant residue was purified by silica gel column chromatography (Eluent: hexane)

ORD record

ord-4350711110db497eb7425289eeef9df6

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604069B2