Synlett 2010(14): 2204-2205  
DOI: 10.1055/s-0030-1258020
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Bromotrichloromethane

Fanny Cros*
Laboratoire de Chimie Organique-Photochimie et Synthèse, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, UMR CNRS 5246, Université Claude Bernard Lyon 1, 69622 Villeurbanne, France
e-Mail: fanny.cros@gmail.com;
Further Information

Publication History

Publication Date:
16 August 2010 (online)

Introduction

Readily synthesized by Meunier et al. [¹] in 1938, bromo­trichloromethane (BrCCl3) is a reagent of choice in organic synthesis. In recent years, many applications of this reagent have been reported. It can be used to synthesize esters, oxidize heterocycles, allow alkoxyl ring-closure reactions, perform α-bromination of sulfones, achieve radical addition on alkenes and radical cyclization of 1,6-dienes or synthesize dichloroalkenes. Some of these reactions were used at a final stage of complex total syntheses. Moreover, bromotrichloromethane is cheap, commercially available and stable at room temperature without any observed decomposition.

    References

  • 1 Simons JH. Sloat TK. Meunier AC. J. Am. Chem. Soc.  1938,  61:  435 
  • 2 Otera J. Angew. Chem. Int. Ed.  2001,  40:  2044 
  • 3 Lee AS.-Y. Yang H.-C. Su F.-Y. Tetrahedron Lett.  2001,  42:  301 
  • 4 Hwu JR. Hsu C.-Y. Jain ML. Tetrahedron Lett.  2004,  45:  5151 
  • 5a You S.-L. Kelly JW. Tetrahedron Lett.  2005,  46:  2567 
  • 5b Bagley MC. Chapanei K. Dale JW. Xiong X. Bower J. J. Org. Chem.  2005,  70:  1389 
  • 6a Mislin GL. Burger A. Abdallah MA. Tetrahedron  2004,  60:  12139 
  • 6b Bowers AA. West N. Newkirk TL. Troutman-Youngman AE. Schreiber SL. Wiest O. Bradner JE. Williams RM. Org. Lett.  2009,  11:  1301 
  • 7 Chorell E. Das P. Almqvist F. J. Org. Chem.  2007,  72:  4917 
  • 8a Hartung J. Knever R. Eur. J. Org. Chem.  2000,  1677 
  • 8b Hartung J. Knever R. Tetrahedron: Asymmetry  2003,  14:  3019 
  • 9 Meyers CY. Chan-Yu-King R. Hua DH. Kolb VM. Matthews WS. Parady TE. Horii T. Sandrock PB. Hou Y. Xie S. J. Org. Chem.  2003,  68:  500 
  • 10 Heintz M. Le NyC. Nedelec JY. Tetrahedron Lett.  1984,  25:  5767 
  • 11 Mirzabekova NS. Kuz’mina NE. Lukashov OI. Sokolova NA. Golosov SN. Kazakov PV. Perlova TG. Potapova VV. Kheinman VA. Ivanova GB. Russ. J. Org. Chem.  2008,  44:  1139 
  • 12a Gilbert BC. Parsons AF. J. Chem. Soc., Perkin Trans. 2  2002,  367 
  • 12b Huther N. McGrail PT. Parsons AF. Eur. J. Org. Chem.  2004,  1740 
  • 13 Nenajdenko VG. Shastin AV. Muzalevskii VM. Balenkova ES. Russ. Chem. Bull., Int. Ed.  2004,  2647