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30th August 2013 @ 13:55

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Reaction information

*#Reaction file  
Scheme_412.cdx
*Reaction file type CDX
*Procedure  N-Allyl-N-(3-bromo-3-butenyl)-N-methylamine (413, 1.0 mmol, 203 mg) was added to a 25 mL flask.  The flask was fitted with a reflux condenser, septum and flushed with argon.  Dry THF (10.0 mL) was added under argon, followed by benzeneboronic acid (244 mg, 2.0 mmol) and PdCl2(PPH3) (0.10 mol eq., 70.0 mg).  To this yellow solution was added a saturated solution of Na2CO3 (30.0 mL), the mixture was then heated for 12 hours at 70 °C.  When the reaction was deemed to be complete (absence of vinyl bromide by tlc) the crude reaction mixture was extracted into Et2O (50.0 mL).  The combined organic layer was washed with water (3 x 50 mL), brine (50.0 mL), dried over MgSO4, filtered and removal of solvent.  Column chromatography (SiO2, 0-100 % Et2O:petroleum ether including 5 % Et3N) afforded the title compound as a yellow oil (131 mg, 0.65 mmol, 65 %).  Carried out based on a procedure developed by Johnson and Johns
*Yield (%)  65
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp150.pdf
DM Thesis_2000_pp64.pdf
Further information  

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Overall reaction? True
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Attached Files
DM Thesis_2000_pp64.pdf
DM Thesis_2000_pp150.pdf
Scheme_412.cdx