D.J. Adams et al. / Journal of Fluorine Chemistry 94 (1999) 51±55
55
the expected material, with almost all the material uniden-
Acknowledgements
ti®able in some cases. This can be attributed to the solubility
of the phenols in the aqueous layer in some cases when
washing the samples in DCM prior to GC analysis. To verify
this, a sample of 2-hydroxy-6-¯uoro benzonitrile (synthe-
sised from 2,6-di¯uorobenzonitrile using TMAOH in
DMSO and DCM) was washed once with 1 M HCl solution
and twice with water to replicate a typical sample work up.
After the third wash, only 45% of the initial phenol was still
identi®able by GC.
We thank Victrex PLC for ®nancial support (to DA and
HM), the EPSRC Clean Technology Unit for a studentship
(to DN), the Royal Academy of Engineering/EPSRC for a
Clean Technology Fellowship (to JHC) and other members
of the York Clean Synthesis Group for their collaboration.
We would also like to thank Dr. Keith Martin for the Karl
Fischer analysis.
4-Chloro, 3-nitro-N-(4-cyano-2-nitrophenyl)benzamide:
MS (m/z, %) 346 (13); 300 (3); 184 (100); 138 (38); 110
(24); 75 (17); H-NMR (CDCl3) ꢀ 11.65 (NH, s), 9.19 (d),
References
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1546 (s), 1512 (s), 1459 (m), 1351 (m), 1288 (m).
2-Fluoro-6-hydroxybenzonitrile: MS (m/z, %) 137 (83),
109 (100), 89 (9), 82 (28), 63 (10); 1H-NMR (DMSO-d6) ꢀ
11.58 (OH, broad), 7.52 (d.t), 6.87 (d), 6.85 (t) ppm; 13C-
NMR (DMSO-d6) ꢀ 167.2 (d), 165.7 (d), 139.8 (d), 116.6
(d), 92.9 (d) ppm; 19H-NMR (DMSO-d6, CFCl3 as internal
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1463 (s), 1352 (s), 1318 (s), 1245 (m), 1180 (w), 1166 (m),
1020 (s), 791 (s), 723 (m), 664 (m), 557 (w), 523 (w).
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N, 10.2%. Found: C, 60.19%; H, 2.75%; N, 10.11%;
m.p.1648C.
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N-(2-cyano-3-¯uorophenyl)-2,6-di¯uorobenzamide: MS
(m/z, %) 276 (17), 141 (100), 113 (23), 63 (13); IR (KBr
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2231 (w, CN), 1686 (m), 1666 (m), 1626 (m), 1592 (m),
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