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22nd August 2013 @ 15:11

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Reaction information

*#Reaction file
reactionscheme_3 .cdx
*Reaction file type CDX
*Procedure A stirred solution of S-4-Iodothiophenyl-N,N-dimethylcarbamate (5.3 g, 17.2 mmol) and KOH (2.9 g, 51.7 mmol, 3.00 eq.) in degassed MeOH (100 mL), in a 250 mL rbf, was heated to reflux (80 ºC) for 1 h. The reaction vessel was then cooled in an ice bath and a solution of 2 M HCl (aq.) was added dropwise until the pH of the reaction mixture was approx. 1, followed by the addition of water (60 mL). The resulting suspension was suction-filtered through filter paper and washed with a large amount of water, which was then extracted three times with Et2O. The combined organic phases were dried over anhydrous MgSO4 and vacuum evaporated to afford a mixture of product (4.0 g, 16.9 mmol, yield 98%) (Rf 0.66) and a small amount of dimerization by-product (trace on TLC; Rf 0.78, (1/1) hexane/DCM).
*Yield (%) 98 %
*Type of Yield Reaction yield
Reference(s)
PhD Thesis - 16Sep2010_final p11.pdf
PhD Thesis - 16Sep2010_final p106.pdf
Further information 4-Iodothiophenol

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 2: Rearrangement from O-carbamate to S-carbamate: S-4-Iodothiophenyl-N,N-dimethylcarbamate
For step in multistep reaction - link to following reaction step Reaction 4: Substitution of 4-Iodothiophenol with acetyl chloride: 1-acetylthio-4-iodobenzene
Attached Files
PhD Thesis - 16Sep2010_final p106.pdf
reactionscheme_3 .cdx