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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