COMMUNICATIONS
Luigi Aurelio et al.
combined organic layers were dried (MgSO4), filtered and
concentrated to a brown/red viscous oil. The crude material
was chromatographed on silica gel eluting with 5% diethyl
ether in petroleum spirits, providing 20 as a viscous amber
oil; yield: 3.74 g (7.79 mmol, 78% from 2-iodoaniline).
1H NMR (400 MHz, CDCl3): d=7.75–7.68 (m, 2H), 7.68–
7.61 (m, 1H), 7.53–7.44 (m, 3H), 7.33–7.26 (m, 3H), 2.37 (s,
3H); 13C NMR (101 MHz, CDCl3): d=169.2, 137.9, 135.7,
135.1, 133.7, 131.3, 130.2, 128.9, 126.0, 123.5, 122.1, 113.9,
82.8, 20.6. LC-MS: Rf (min)=7.48; MS: m/z=394.0 (M+
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H);
HR-MS
(ESI):
m/z=415.9575,
calcd.
for
C16H12INNaOS+ (M+Na): 415.9576.
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[13] TBAI and excess I2 were removed by aqueous wash
(Na2S2O3) during extractive work-up.
1978
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Adv. Synth. Catal. 2014, 356, 1974 – 1978