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22nd August 2013 @ 15:50

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Reaction information

*#Reaction file
reactionscheme_4 .cdx
*Reaction file type CDX
*Procedure To a vigorously stirred solution of 4-Iodothiophenol (2.36 g, 10.0 mmol) in pyridine (30 mL), in a 50 mL Schlenk flask and under Ar atmosphere, was added acetyl chloride (1.42 mL, 1.57 g, 20.0 mmol, 2.00 eq.) dropwise over 15 minutes. The mixture was quenched with crushed ice and water to obtain a suspension that was vac-filtered. The white solid was washed with water, dissolved in Et2O and dried over anhydrous MgSO4, to afford after evaporation of the solvent the crude title compound (2.30 g). The product was column chromatographed on silica gel using as eluent (1/1) hexane/DCM; after recrystallization from (1/1) MeOH/water it was washed with water, dissolved in Et2O, dried over anhydrous MgSO4 and dried under vacuum. The pure product was obtained as white microcrystalline powder (2.03 g, 7.30 mmol, yield 73%).
*Yield (%) 73 %
*Type of Yield Isolated pure product
Reference(s)
PhD Thesis - 16Sep2010_final p11.pdf
PhD Thesis - 16Sep2010_final p106.pdf
Further information 1-Acetylthio-4-iodobenzene

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 3: Removal of S-carbamate protecting group: 4-Iodothiophenol
For step in multistep reaction - link to following reaction step  
Attached Files
reactionscheme_4 .cdx