Synthesis 2019; 51(16): 3055-3059
DOI: 10.1055/s-0037-1611526
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© Georg Thieme Verlag Stuttgart · New York

A Practical, Large-Scale Synthesis of p-(Difluoroiodo)toluene (p-TolIF2)

Jason Tao
,
Department of Chemistry, University of Waterloo, 200 University Ave. W., Waterloo, ON, N2L 3G1, Canada   Email: [email protected]
› Author Affiliations
This work was supported by the Natural Sciences and Engineering Research Council of Canada (NSERC; grant number 418602-2013) and by the University of Waterloo. J.T. was supported by an NSERC PGS-D award.
Further Information

Publication History

Received: 06 March 2019

Accepted after revision: 26 March 2019

Publication Date:
25 April 2019 (online)


Abstract

p-(Difluoroiodo)toluene (p-TolIF2) is a versatile fluorinating agent that acts as both a surrogate for elemental fluorine, and as a source of ‘electrophilic’ fluorine. Described here is a detailed three-step synthesis of p-TolIF2, carried out on a 50 mmol scale, that consistently provides high-quality product that is suitable for long-term storage. The reactions employ inexpensive, readily available starting materials and reagents, and uses the commodity chemical 48% aqueous HF as the source of fluorine atoms.

Supporting Information

 
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