European Journal of Organic Chemistry
10.1002/ejoc.201900237
FULL PAPER
[
39]
1
5
-Chloro-2-hydroxybenzoic acid 2p.
Tan solid, Mp = 168-170ºC;. H
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H. Shi, P. Wang, S. Suzuki, M. E. Farmer, J.-Q. Yu, J. Am. Chem. Soc.
2016, 138, 14876-14879.
NMR (360 MHz, CDCl
3
) δ 7.01 (1H, d, J = 8.6 Hz), 7.50 (1H, dd, J = 8.6
Hz, J = 2.0 Hz), 7.92 (1H, d, J = 2.0 Hz); isolated yield: 5.67 g (77%) from
[10] M. A. B. Mostafa, R. M. Bowley, D. T. Racys, M. C. Henry, A.
6.00 g of 1p.
Sutherland, J. Org. Chem. 2017, 82, 7529-7537.
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[
10]
1
2
-Chloro-4-nitrophenol 2q. White off solid, Mp = 106-108 ºC; H NMR
) δ 6.22 (1H, s), 7.16 (1H, d, J = 8.1 Hz), 8.16 (1H, dd, J
8.1 Hz, J = 2.0 Hz), 8.32 (1H, d, J = 2.0 Hz); isolated yield: 61 mg
(360 MHz, CDCl
3
=
[
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(
39%) from 125 mg of 1q.
[
40] 1
2
4
s).
-Chloro-4-(trifluoromethyl)aniline 2r.
.26 (2H, bs), 6.78 (1H, d, J = 8.2 Hz), 7.29 (1H, d, J = 8.2 Hz), 7.53 (1H,
3
H NMR (250 MHz, CDCl ) δ
8
1, 6066-6074.
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[
41]
4
-Bromo-2-chloro-N,N-dimethylaniline 2s.
Tan solid, Mp. = 110-112
) δ 2.81 (6H, s), 6.94 (1H, d, J = 7.2 Hz),
.33 (1H, dd, J = 7.2 Hz, J = 2.0 Hz), 7.51 (1H, d, J = 2.0 Hz); isolated
yield: 228 mg (78%) from 250 mg of 1s.
1
ºC; H NMR (360 MHz, CDCl
7
3
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32, 1798-1799. b) W. Guo, E. Faggi, R. M. Sebastián, A. Vallribera, R.
[
42]
3
-Chloro-4-(dimethylamino)benzaldehyde 2t.
Tan solid, Mp = 72-73
Pleixats, A. Shafir, J. Org. Chem. 2013, 78, 8169-8175. c) Z. Jia, E.
Gálvez, R. M. Sebastián, R. Pleixats, A. Álvarez-Larena, E. Martin, A.
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ºC; H NMR (360 MHz, CDCl
6
3
) δ 2.98 (6H, s), 7.08 (1H, d, J = 9.8 Hz),
.70 (1H, dd, J = 9.8 Hz, J = 3.6 Hz), 7.85 (1H, d, J = 3.6 Hz), 9.82 (1H,
s); isolated yield: 480 mg (78%) from 500 mg of 1t.
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We are thankful for financial support from Spain’s MICINN
2841-2844.
(
Grants CTQ2014-53662-P) and MEC (CTQ2016-81797-REDC).
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1
Keywords: PIFA • TMSCl • arene • electrophilic chlorination •
2
I(III) species
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