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20th August 2013 @ 11:35

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Reaction information

*#Reaction file
reactionscheme_40 .cdx
*Reaction file type CDX
*Procedure Repeating the standard Friedel-Crafts acylation procedure, 2,5-dibromobenzene (7.08 g, 30.0 mmol) and AlCl3 (4.00 g, 30.0 mmol, 1.00 eq.) were ground and placed in a 50 mL Schlenk flask fitted with a condenser; after the evacuation/refill with Ar cycle, the top Schlenk arm was replaced with an oil bubbler. AcCl (2.13 mL, 30.0 mmol, 1.00 eq.) was then added, and the mixture was heated to 120 °C; before all of the solid had been washed down by the refluxing AcCl (Bp 52 °C), the solution turned dark-green (after 10 minutes). After 2 hours the reaction, containing both unreacted starting material (as monitored by GC, SD_FASTD, RT 3.0 min) and product (RT 4.7 min), was let cooling to r.t. and HCl (2N) was added slowly  (with shaking) until the evolution of gas stopped. The aqueous phase was extracted with Et2O (3 x 50 mL), the combined organic phases where washed again with HCl (2N, 50 mL) and dried over MgSO4. Evaporation of the solvent afforded the crude product (brown oil, 7.070 g) that was column chromatographed on silica gel using (10/1) hexane/Et2O to yield the partially pure title compound (brownish solid, Rf 0.26; 1.694 g). This was dissolved in hot hexane, let cool to r.t. and then in ice, to obtain, after filtration and evaporation, the pure product (white flakes, 1.35 g, 4.86 mmol, yield 16 %).
*Yield (%) 16 %
*Type of Yield Isolated pure product
Reference(s)
PhD Thesis - 16Sep2010_final p19.pdf
 
PhD Thesis - 16Sep2010_final p129.pdf
Further information Compound 40: 2,5-dibromoacetophenone

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  
For step in multistep reaction - link to following reaction step Reaction 41: Oxidation of 2,5-dibromoacetophenone: 2,5-Dibromobenzoic acid
Attached Files
reactionscheme_40 .cdx
PhD Thesis - 16Sep2010_final p19.pdf
PhD Thesis - 16Sep2010_final p129.pdf