Molecules 2019, 24, 3720
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cessation of effervescence. The organic layer was separated and dried over anhydrous Na2SO4 and
concentrated in vacuo affording a clear liquid which was purified by column chromatography on silica
1
gel (n-hexane/ethyl acetate 5:1) to give clear liquid (0.622 g, 76%). H NMR (400 MHz, Chloroform-d)
δ
8.00 (d, J = 7.7 Hz, 1H), 7.47–7.39 (t, J = 7.7 Hz, 1H), 7.27 (t, J = 7.7 Hz, 1H), 7.22 (d, J = 7.7 Hz, 1H), 2.93
(t, J = 6.0 Hz, 2H), 2.62 (t, J = 6.0 Hz, 2H), 2.10 (p, J = 6.4 Hz, 2H); 13C NMR (101 MHz, Chloroform-d)
δ
198.22, 144.36, 133.26, 132.47, 128.65, 126.99, 126.47, 39.02, 29.56, 23.15.
p-Ethoxychlorobenzene 2 [20]: clear liquid, 1.13 g (93%); 1H NMR (400 MHz, Chloroform-d) δ 7.17–7.08
(m, 2H), 6.75–6.67 (m, 2H), 3.88 (q, J = 7.0 Hz, 2H), 1.30 (t, J = 7.0 Hz, 3H); 13C NMR (101 MHz,
Chloroform-d) δ 157.55, 129.24, 125.31, 115.72, 63.71, 14.72.
Ethoxy-2,4-dichlorobenzene
3 [ δ 7.27 (d,
25]: clear liquid, 0.91 g (78%); 1H NMR (400 MHz, Chloroform-d)
J = 2.6 Hz, 1H), 7.07 (dd, J = 8.8, 2.6 Hz, 1H), 6.73 (d, J = 8.8 Hz, 1H), 3.98 (q, J = 7.0 Hz, 2H), 1.37 (t, J =
7.0 Hz, 3H); 13C NMR (101 MHz, Chloroform-d)
14.59.
δ 153.28, 129.89, 127.46, 125.42, 123.59, 113.96, 65.00,
p-Ethoxynitrobenzene 4 [ δ 8.18
10]: pale yellow solid, 0.87 g (72%); 1H NMR (400 MHz, Chloroform-d)
(d, J = 9.1 Hz, 2H), 6.93 (d, J = 9.1 Hz, 2H), 4.12 (q, J = 6.9 Hz, 2H), 1.45 (t, J = 7.0 Hz, 3H). 13C NMR
(101 MHz, Chloroform-d) δ 164.03, 125.92, 114.35, 64.40, 14.55.
o-Ethoxyfluorobenzene
5
[
26]: clear liquid, 0.74 g (59%); 1H NMR (400 MHz, Chloroform)
δ
6.86–7.11 (m,
4H), 4.11 (q, J = 7.0 Hz, 2H), 1.46 (t, J = 7.0 Hz, 3H);13C NMR (101 MHz, Chloroform-d)
δ
152.75 (d, JC-F
= 245.25), 146.95 (d, JC-F = 10.12), 124.20 (d, JC-F = 3.89), 120.85 (d, JC-F = 7.00), 116.08 (d, JC-F = 17.91),
114.84 (d, JC-F = 1.55), 64.80, 14.75.
1
Ethoxy-2,6-difluorobenzene
6
[
27]: clear liquid, 0.63 g (51.7%); H NMR (400 MHz, Chloroform-d)
δ
δ
6.98–6.73 (m, 3H), 4.18 (qm, J = 7.0, 2H), 1.37 (t, J = 7.0, 3H); 13C NMR (101 MHz, Chloroform-d)
156.41 (dd, JC-F = 248.34, 5.45), 135.44 (t, JC-F = 14.41), 122.60 (t, JC-F = 9.34), 112.04 (dd, JC-F = 16.35,
6.23), 64.80, 14.75.
p-Ethoxytoluene
7 [ δ 7.02–6.95 (m,
21]: clear liquid, 1.11 g (88%); 1H NMR (400 MHz, Chloroform-d)
2H), 6.75–6.67 (m, 2H), 3.91 (q, J = 7.0, 2H), 2.19 (s, 3H), 1.31 (t, J = 7.0, 3H); 13C NMR (101 MHz,
Chloroform-d) δ 156.76, 129.82, 129.64, 114.28, 63.36, 20.41, 14.85.
o-Ethoxytoluene 8 [ δ 7.56–7.46 (m, 2H),
21]: clear liquid, 0.67 g (53%); 1H NMR (400 MHz, Chloroform-d)
7.26–7.13 (m, 2H), 4.39 (q, J = 7.0 Hz, 2H), 2.61 (s, 3H), 1.79 (t, J = 7.0 Hz, 3H); 13C NMR (101 MHz,
Chloroform-d) δ 159.02, 139.40, 129.18, 121.38, 115.40, 111.38, 63.23, 21.52, 14.90.
m-Ethoxytoluene
9 [4 δ 7.19 (t, J = 8.1 Hz,
]: clear liquid, 1.13 g (90%); 1H NMR (400 MHz, Chloroform-d)
1H), 6.56–6.46 (m, 3H), 4.03 (q, J = 7.0 Hz, 2H), 3.80 (s, 3H), 1.43 (t, J = 7.0 Hz, 3H); 13C NMR (101 MHz,
Chloroform-d) δ 159.02, 139.40, 129.18, 121.38, 115.40, 111.38, 63.23, 21.52, 14.90.
p-Ethoxyaniline 10 [ δ 6.69–6.62
28]: light yellow liquid, 0. 21 g (17%); 1H NMR (400 MHz, Chloroform)
(m, 2H), 6.55 (d, J = 8.7 Hz, 2H), 3.87 (q, J = 7.0 Hz, 2H), 3.26 (bs, 2H), 1.29 (t, J = 7.0 Hz, 3H); 13C NMR
(101 MHz, Chloroform-d) δ 152.13, 139.79, 116.44, 115.67, 64.04, 14.95.
α
-Ethoxynaphthalene 11 [ δ 7.64–7.82
28]: clear liquid, 0.88 g (74%);1H NMR (400 MHz, Chloroform-d)
(m, 3H), 7.47–7.51 (m, 1H), 7.36–7.40 (m, 1H), 7.16–7.23 (m, 2H), 4.26 (q, J = 6.85 Hz, 2H), 1.64 (t, J =
6.85 Hz, 3H); 13C NMR (101 MHz, Chloroform-d)
δ 156.9, 134.59, 129.29, 128.87, 127.59, 126.67, 126.23,
123.44, 118.96, 106.51, 63.35, 14.75.
β
-Ethoxynaphthalene 12 [4, δ 8.47–8.50
23]: clear liquid, 1.01 g (85%);1H NMR (400 MHz, Chloroform-d)
(m, 1H), 7.91–7.93 (m, 1H), 7.46–7.63 (m, 4H), 6.87 (d, J = 7.83 Hz, 1H), 4.26 (q, J = 7.0 Hz, 2H), 1.64
(t, J = 7.0 Hz, 3H); 13C NMR (101 MHz, Chloroform-d)
δ 154.70, 134.47, 127.35, 126.23, 125.85, 125.70,
124.96, 122.06, 119.93, 104.51, 63.55, 14.74.