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20th August 2013 @ 11:40

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Reaction information

*#Reaction file
reactionscheme_41 .cdx
*Reaction file type CDX
*Procedure Following a procedure reported by Vogel, 2,5-dibromoacetophenone (1.35 g, 4.86 mmol)  was dissolved in dioxane (7 mL, ~ 5 mL/g) and added dropwise to a NaClO solution (‘bleach’) pre-heated to 50 °C. The mixture was then heated to 75 °C and let stirring for ½ h, time sufficient for the complete disappearance of starting material to occur (Rf 0.50 in 1/1 hexane/Et2O). After cooling to r.t., water (50 mL) was added, followed by Na2S2O3 (20% aq., 25 mL) to quench the excess oxidizer (confirmed by negative reaction on starch/I- paper). The mixture, strongly basic, was washed with Et2O (50 mL), then acidified until pH 1 with HCl (2N, 100 mL), resulting in the formation of a white flocculate. This was separated by vacuum filtration, washed with iced water and dried; the solid was dissolved in a small volume of Et2O and loaded onto silica gel, then column chromatographed through a short silica plug using 1/1 hexane/Et2O as eluent (product Rf 0.75). Evaporation of the solvent afforded the title compound (white solid, 1.116 g, 3.99 mmol, yield 82 %) that was not purified further.
*Yield (%) 82 %
*Type of Yield Reaction yield
Reference(s)

PhD Thesis - 16Sep2010_final p19.pdf
 
PhD Thesis - 16Sep2010_final p129-130.pdf

Vogel’s Textbookof Practical Organic Chemistry” Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A.R. (Longman Scientific and Technical, UK, 5th edition).

Further information Compound 41: 2,5-Dibromobenzoic acid

For multistep reactions (or their steps):

Overall reaction? False
For overall reaction - links to child reaction steps  
For step in multistep reaction - link to previous reaction step Reaction 40: Friedal-Crafts acylation: 2,5-dibromoacetophenone
For step in multistep reaction - link to following reaction step Reaction 42: Sonogashira coupling: 2,5-bis(2-(4-(methylthio)phenyl)ethynyl)benzoic acid
Attached Files
PhD Thesis - 16Sep2010_final p129-130.pdf
reactionscheme_41 .cdx
PhD Thesis - 16Sep2010_final p19.pdf