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30th August 2013 @ 13:58

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Reaction information

*#Reaction file  
*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 1-naphthaleneboronic acid (344.0 mg, 2.0 mmol) and PdCl2(PPH3) (0.10 mol, 70.0 mg).  To this yellow solution was added a saturated solution of Na2CO3 (30 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 the solvent removed under reduced pressure.  Column chromatography (SiO2, 0-100 % Et2O:petroleum including 5 % Et3N) afforded the title compound as an light orange oil (171 mg, 0.68 mmol, 68 %).  Carried out based on a procedure developed by Johnson and Johns
*Yield (%)  68
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp64.pdf
DM Thesis_2000_pp151.pdf
Further information  

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Overall reaction? True
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Attached Files
DM Thesis_2000_pp64.pdf
DM Thesis_2000_pp151.pdf