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Efficient continuous-flow bromination of methylsulfones and methanesulfonates and continuous synthesis of hypobromite

(2014) JOURNAL OF FLOW CHEMISTRY. 4(3). p.118-124
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Abstract
An efficient continuous-flow procedure for the synthesis of tribromomethylsulfones and tribromomethanesulfonates has been developed starting from the corresponding methylsulfones or methanesulfonates and potassium hypobromite using a biphasic reaction. Two different continuous-flow systems were used and compared for the bromination reaction. Different derivatives were synthesized in excellent isolated yields in very short reaction times using a small excess of potassium hypobromite. Hypobromite can be synthesized continuously leading to the continuous production of the brominated derivates. With the optimized flow conditions, a throughput of up to 53 g/day was obtained. The bromination reaction in flow has significant advantages compared to the corresponding batch process.
Keywords
MASS-TRANSFER, MICROSTRUCTURED REACTORS, MICROREACTOR, SULFONE, SULFONAMIDES, SULFIDE, ACID, TRANSFER-CATALYZED ESTERIFICATION, hypobromite, bromination, methanesulfonates, methylsulfones, continuous flow

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Citation

Please use this url to cite or link to this publication:

MLA
Van Waes, Frederik et al. “Efficient Continuous-flow Bromination of Methylsulfones and Methanesulfonates and Continuous Synthesis of Hypobromite.” JOURNAL OF FLOW CHEMISTRY 4.3 (2014): 118–124. Print.
APA
Van Waes, F., Seghers, S., Dermaut, W., Cappuyns, B., & Stevens, C. (2014). Efficient continuous-flow bromination of methylsulfones and methanesulfonates and continuous synthesis of hypobromite. JOURNAL OF FLOW CHEMISTRY, 4(3), 118–124.
Chicago author-date
Van Waes, Frederik, Sofie Seghers, Wim Dermaut, Bart Cappuyns, and Christian Stevens. 2014. “Efficient Continuous-flow Bromination of Methylsulfones and Methanesulfonates and Continuous Synthesis of Hypobromite.” Journal of Flow Chemistry 4 (3): 118–124.
Chicago author-date (all authors)
Van Waes, Frederik, Sofie Seghers, Wim Dermaut, Bart Cappuyns, and Christian Stevens. 2014. “Efficient Continuous-flow Bromination of Methylsulfones and Methanesulfonates and Continuous Synthesis of Hypobromite.” Journal of Flow Chemistry 4 (3): 118–124.
Vancouver
1.
Van Waes F, Seghers S, Dermaut W, Cappuyns B, Stevens C. Efficient continuous-flow bromination of methylsulfones and methanesulfonates and continuous synthesis of hypobromite. JOURNAL OF FLOW CHEMISTRY. 2014;4(3):118–24.
IEEE
[1]
F. Van Waes, S. Seghers, W. Dermaut, B. Cappuyns, and C. Stevens, “Efficient continuous-flow bromination of methylsulfones and methanesulfonates and continuous synthesis of hypobromite,” JOURNAL OF FLOW CHEMISTRY, vol. 4, no. 3, pp. 118–124, 2014.
@article{6855029,
  abstract     = {An efficient continuous-flow procedure for the synthesis of tribromomethylsulfones and tribromomethanesulfonates has been developed starting from the corresponding methylsulfones or methanesulfonates and potassium hypobromite using a biphasic reaction. Two different continuous-flow systems were used and compared for the bromination reaction. Different derivatives were synthesized in excellent isolated yields in very short reaction times using a small excess of potassium hypobromite. Hypobromite can be synthesized continuously leading to the continuous production of the brominated derivates. With the optimized flow conditions, a throughput of up to 53 g/day was obtained. The bromination reaction in flow has significant advantages compared to the corresponding batch process.},
  author       = {Van Waes, Frederik and Seghers, Sofie and Dermaut, Wim and Cappuyns, Bart and Stevens, Christian},
  issn         = {2062-249X},
  journal      = {JOURNAL OF FLOW CHEMISTRY},
  keywords     = {MASS-TRANSFER,MICROSTRUCTURED REACTORS,MICROREACTOR,SULFONE,SULFONAMIDES,SULFIDE,ACID,TRANSFER-CATALYZED ESTERIFICATION,hypobromite,bromination,methanesulfonates,methylsulfones,continuous flow},
  language     = {eng},
  number       = {3},
  pages        = {118--124},
  title        = {Efficient continuous-flow bromination of methylsulfones and methanesulfonates and continuous synthesis of hypobromite},
  url          = {http://dx.doi.org/10.1556/JFC-D-14-00006},
  volume       = {4},
  year         = {2014},
}

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