Continuous microflow bromination of alkenes combined with a circulatory recycling of a fluorous polyether as a bromine support

Journal of Flow Chemistry

Volumn 3, Issue 1, 2013, Pages 4-6

  Fukuyama, T ^a   Rahman, Md T ^a   Kamata, N ^a   Tokizane, M ^a   Fukuda, Y ^a   Ryu, I ^a  

^a Osaka City University   (Japan)

Author keywords

bromination; circulatory flow system; fluorous solvent; microreactor

Indexed keywords

EID: 84883400093     PISSN: 2062249X     EISSN: 20630212     Source Type: Journal    
DOI: 10.1556/JFC-D-12-00023     Document Type: Article

References (34)

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31. Continuous microflow bromination of cyclohexene with a circulatory recycling of Galden: a hexane solution of cyclohexene (75 mmol, 6.16 g) was loaded into a container (0.75 M, 100 mL). Galden HT135 (50 mL), bromine (excess), and water were loaded into another container.
32. Saturated Br2 solution in Galden HT135 was prepared with gentle stirring. Flow rates were adjusted to 0.15 mL/min for cyclohexene solution and 1.2 mL/min for saturated bromine solution, and the two solutions were mixed in a T-shaped micromixer (MiChS® 400, 400 m i.d.).
33. The mixture was then fed into the residence time unit (500m i.d. × 3.4 m, residence time: 2 min). The reaction mixture was then mixed with 0.3Mbasic Na2S2O3 aqueous solution in another T-shaped mixer (MiChS® 400, 400 m i.d.), and the entire mixture was collected in a Y-shaped flask, where a small amount of CHCl3 was placed. The bottomed fluorous solvent was pumped back to the container containing bromine.
34. This system was operated for 6 hours, and consumed 40.5 mmol of cyclohexene. The top organic phase was separated from the aqueous phase, and the aqueous phase was extracted with hexane. Combined organic phase was dried over MgSO4. The solvent was removed under reduced pressure to give colorless oil (8.91 g), which was purified by short silica gel column chromatography to give pure dibromocyclohexane (8.3 g, 85).