Primary Alkyl Bromides from Dimethylthiocarbamates

Abstract

The conversion of primary alkyl dimethylthiocarbamates into alkyl bromides using the Vilsmeier reagent occurs in high yields in the presence of other non-acid sensitive and non-nucleophilic functional groups.

halogenation - protecting groups - alkyl halides - thiocarbamates - Vilsmeier

References

1 Greene TW. Wuts PG. In Protective Groups in Organic Synthesis   3rd ed.:  Wiley; New York: 1999. 

2 Barton DHR. Stick RV. Subramanian R. J. Chem. Soc., Perkin Trans. 1  1976,  2112 

3 Cristol SJ. Seapy DG. J. Org. Chem.  1982,  47:  132 

4 Barbier F. Pautrat F. Quiclet-Sire B. Zard SZ. Synlett  2002,  811 

5 Koen MJ. Le Guyader F. Motherwell WB. J. Chem. Soc., Chem. Commun.  1995,  1241 

6 Gade AM. Abelt CJ. Synthesis  2007,  2097 

7 Barma DK. Bandyopadhyay A. Capdevila JH. Falck JR. Org. Lett.  2003,  5:  4755 

8 Fikse MA. Bylund WE. Holubowitch NE. Abelt CJ. Synthesis  2006,  4118 

9 Schlama T. Gouverneur V. Mioskowski C. Tetrahedron Lett.  1997,  38:  3517 

10 Jones G. Stanforth SP. Org. React.  2000,  56:  355