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2nd September 2013 @ 09:25

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Reaction information

*#Reaction file
reactionscheme_38m.cdx
*Reaction file type CDX
*Procedure

To a 30 mL Schlenk vial under argon at room temperature was added dppf (67.7 mg, 0.12 mmol), sodium phenoxide (3.5 mL of a 1.7 M soln. in THF), PhBr (0.20 g, 1.3 mmol) and n-BuNC (0.20 mL, 2.0 mmol). PdCl2 (11.9 mg, 0.068 mmol) was then added against a counterflow of argon. Finally, dry toluene (7 mL) was used to wash all solids from the sides of the vial, which was then heated at 109 °C in a Stem block for 5 h.The reaction mixture was allowed to cool to room temperature before water (20 mL) was added. The organic layer was separated and the aqueous solution extracted with ether (4x15 mL). The combined organics were dried over MgSO4, filtered and evaporated. Further purification on silica with petrol : ether (4:1 + 5% NEt3) gave the title compound as a pale-yellow oil, (0.21 g, 68%).

*Yield (%) 68 %
*Type of Yield Isolated pure product
Reference(s)
Gustaf Saluste p114-115.pdf
Further information  

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Overall reaction? True
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Attached Files
Gustaf Saluste p114-115.pdf
reactionscheme_38m.cdx