The Journal of Organic Chemistry
Article
3-Fluoroacetophenone (3h).22 3h was also prepared from 3-
acetylphenylboronic acid (1m) (0.34 g, 2.1 mmol) as described above
using 2 molar equiv of AcOF solution. A colorless liquid (0.17 g, 60%
yield) was obtained.
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4-Fluorobenzonitrile (2i)23 and 3-Fluorobenzonitrile (3i).24
2i and 3i were formed as a mixture of products in a 3:1 ratio,
respectively, from 4-cyanophenylboronic acid (1i) (0.41 g, 2.8 mmol)
as described above using 2.5 molar equiv of AcOF solution (Table 2
and Supporting Information). Compound 3i was also obtained from
the reaction of 3-cyanophenylboronic acid (1n) (0.35 g, 2.4 mmol) as
described above using 3.5 molar equiv of AcOF solution. A colorless
liquid (0.22 g, 75% yield) was obtained.
4-Fluoronitrobenzene (2j)25 and 3-Fluoronitrobenzene
(3j).19 2j and 3j were formed as a mixture of products in a 3:2
ratio, respectively, from 4-nitrophenylboronic acid (1j) (0.30 g, 1.8
mmol) using 2.5 molar equiv of AcOF solution (Table 2 and
Supporting Information).
4-Fluoro-3-methylbenzonitrile (2l).27 2l was prepared from 4-
cyano-2-methylphenylboronic acid (1l) (0.36 g, 2.3 mmol) as
described above using 2 molar equiv of AcOF solution. A white
solid (0.27 g, 87% yield, mp 59−61 °C) was obtained.
ASSOCIATED CONTENT
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S
* Supporting Information
1H, 13C, and 19F NMR spectra and GC data. This material is
AUTHOR INFORMATION
Corresponding Author
*Tel.: 972-3-6408378; Fax: 972-3-6409293; E-mail: rozens@
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Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
This work was supported by the Israel Science Foundation.
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