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30th August 2013 @ 14:17

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Reaction information

*#Reaction file  
Scheme_421.cdx
*Reaction file type CDX
*Procedure  Allyl-benzyl-(3-bromo-but-3-enyl)-amine (420, 2.0 mmol, 560 mg) was added to a 25 mL flask, 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 mmol., 70.0 mg).  To this yellow solution was added a saturated solution of Na2CO3 (40.0 mL.), the mixture heated at 70 °C for 12 hours.  When the reaction was complete (absence of vinyl bromide by tlc) the product was extracted into Et2O (3 x 50.0 mL).  The combined organic layer were 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 (376 mg, 1.36 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_pp193.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_pp193.pdf
Scheme_421.cdx