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9th June 2014 @ 16:28


3-bromo-4-methylbenzenesulfonamide (1.12g, 4.488 mmol)[1], bis(pinacolato)diboron (1.710 g, 6.735 mmol), potassium acetate (1.762 g, 17.96 mmol) was dissolved in 1,4-dioxan (22.5 mL) and degassed with argon for ten minutes. Pd(dppf)2.CH2Cl2 (184 mg, 0.226 mmol) was added and the reaction heated to reflux under argon for 22 hours. The reaction was cooled to room temperature, diluted with methanol (40 mL) and dichloromethane (40 mL). Sonication was used to disperse solids and the resulting mixture was filtered through celite and evaporated under reduced pressure to give a black solid B1 (4.01 g), NMR and TLC indicated consumption of starting material and the appearance of a single new product.[1]

 

NMR and mass spec indicated that this was not the desired product. Starting material to be re-purified or re-synthesised in a purer form.

 

Literature NMR (CDCl3): http://www.sciencedirect.com/science/article/pii/S0960894X10014587

 

Literature M/S (ESI): http://worldwide.espacenet.com/publicationDetails/biblio?CC=US&NR=2006199817&KC=&FT=E&locale=en_EP (page 53)

  

  

Notes:

[1] Material contaminated with an unknown (but substantial) quantity of an insoluble impurity thought to be elemental sulfur. Trying this as a test reaction due to material availability.

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Attached Files
PT-1-20 Scheme.png
PT-20-SM-MeOD.pdf
PT-20-B1-CDCl3.pdf
PT-20-SM-CDCl3.pdf
PT-20-B1-MeOD.pdf
CJCOSDD_ptm20b1_100614_1H_av500.tar
CJCOSDD_ptm20b1cdcl3_110614_1H_av500 (1).tar
CJCOSDD_ptm20smcdcl3_110614_1H_av500 (1).tar
CJCOSDD_ptm20sm_110614_1H_av500.tar
PT-20-B1 ESI-MS.jpg