324
Papers
SYNTHESIS
4-Bromo-2,2¢-bipyridine:27
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8075.
4-Nitro-2,2¢-bipyridyl 1-Oxide:
2,2¢-Bipyridine (15.6 g, 0.1 mol) was oxidized in a mixture of 30%
H2O2 (75 mL) and HOAc (75 mL) by stirring at 60 °C for 12 h. After
the distillation of volatile compounds on a high vacuum pump, the
system was cooled to –4 °C and the residue cautiously dissolved in
concd H2SO4 (40 mL) and nitrated by means of fuming HNO3/concd
H2SO4 (60 mL/40 mL). The product was isolated after 3 h at 100 °C
by precipitation from the neutralized solution (using NaOH pellets)
and recrystallization (EtOH); yield: 6.1 g (28%).
IR: n = 3051 w, 1924 w, 1590 m, 1576 s, 1565 s, 1546 s, 1532 s, 1482
m, 1453 s, 1385 s, 1356 s, 1314 m, 1279 s, 1268 m, 1248 m, 1227 m,
1152 m, 1115 m, 1081 m, 1067 s, 996 s, 884 m, 832 s, 741 s, 726 s,
689 vs, 660 m, 617 s, 587 cm–1 s.
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MS: calcd. for C10H7N3O3 217.18, found m/z 217 (M+., 22%),
(b) Polin, J.; Buchmeiser, M.; Nock, H.; Schottenberger, H.
Mol. Cryst. Liq. Cryst. 1997, 293, 287.
4-Bromo-2,2¢-bipyridine:
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4-Nitro-2,2¢-bipyridyl 1-oxide (2.17 g, 10 mmol) was treated under
reflux with AcBr (40 mL) and PBr3 (10 mL) for 2 h. Neutralization
(using NaOH pellets) and extraction with CH2Cl2 gave the crude
product. The product was isolated after recrystallization (EtOH) as a
white solid; yield: 0.84 g (36%).
MS: calcd. for C10H7BrN2 235.08, found m/z 236, 234 (M+, 100%).
This work has been supported by the Fonds zur Förderung der wis-
senschaftlichen Forschung, Vienna, Austria (J01087-PHY).
a Present Address: KLEMA Dentalprodukte GmbH, Koblacherstr. 3a,
A-6812 Meiningen, Austria
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