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The Royal Society of Chemistry"

Addition of 1,2-ethanedithiol to 2-bromo-1,1-diethoxyethane

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Submitted: May 28, 2010, published: June 1, 2010

Authors

Nikola Paul Chmel (n.chmel@warwick.ac.uk)

A contribution from 

Reaction Scheme

Chemicals

p-toluenesulfonic acid monohydrate
1,2-ethanedithiol
2-bromo-1,1-diethoxyethane

Procedure

Toluene (330 ml) and p-toluenesulfonic acid monohydrate (0.33 g, 1.7 mmol) were heated to reflux in Dean-Stark apparatus under nitrogen for 24 h. The collected water was removed and the Dean-Stark apparatus was replaced with a reflux condenser. 1,2-ethanedithiol (14 ml, 0.167 mol) and 2-bromo-1,1-diethoxyethane (24.5 ml, 0.163 mol) were added and the mixture was heated to reflux for 24 h. The cooled mixture was washed with water (300 ml) and separated. The water layer was back extracted with diethyl ether (3 × 100 ml). The combined organic extracts were washed with brine (3 × 100 ml) and dried twice over anhydrous Na2SO4. The solvents were removed in vacuo and the residue was distilled under vacuum (50°C, 4·10-3 mbar). Yield 6.46 g (34%).

Author Comments

This is an intermediate in the synthesis of BEDT-TSF (BETS).

Data

1H NMR (400 MHz, 298K, CDCl3) δH 6.04 (s, 2H, CH), 3.14 (s, 4H, CH2)

13C NMR (101 MHz, 298K, CDCl3) δC 114.39 (CH), 26.30 (CH2)

Lead Reference

T. Courcet, I. Malfant, K. Pokhodnia and P. Cassoux, New J. Chem., 1998, 22, 585-589

Keywords

addition, alkenes, alkyl/alkenyl/aryl halides, BEDT-TSF, BETS, bisethylenedithiotetraselenafulvalene, elimination, ethers, heterocyclic compounds, nucleophilic, reduction, substitution, sulphides