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The Journal of Organic Chemistry
2-(4-Chlorophenyl)propanenitrile (2h): colorless oil, yield:
87%, 43.1 mg; 1H NMR (400 MHz, CHLOROFORM-D) δ 7.37 (d,
J = 8.6 Hz, 2H), 7.30 (d, J = 8.5 Hz, 2H), 3.88 (q, J = 7.3 Hz, 1H),
1.63 (d, J = 7.3 Hz, 3H); 13C{1H} NMR (101 MHz, CHLOROFORM-
D) δ 135.6, 134.2, 129.4, 128.2, 121.2, 30.8, 21.5. The spectral
data for this compound match that reported in the literature.5
GC-MS:165
2-(Naphthalen-1-yl)propanenitril (2r): colorless oil, yield:
77%, 41.8 mg; H NMR (400 MHz, CHLOROFORM-D) δ 7.91 –
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7.79 (m, 4H), 7.55 – 7.47 (m, 2H), 7.46 – 7.39 (m, 1H), 4.05 (q, J
= 7.3 Hz, 1H), 1.72 (d, J = 7.3 Hz, 3H); 13C{1H} NMR (101 MHz,
CHLOROFORM-D) δ 134.4, 133.4, 132.9, 129.2, 128.0, 127.8,
126.8, 126.6, 125.7, 124.5, 121.7, 31.5, 21.5. The spectral data
for this compound match that reported in the literature.5 GC-
MS:181
2-(4-Fluorophenyl)propanenitrile (2i): colorless oil, yield:
1
61%, 27.3 mg; H NMR (400 MHz, CHLOROFORM-D) δ 7.35 –
2-(6-Methoxynaphthalen-2-yl)propanenitrile (2s): white
1
7.28 (m, 2H), 7.06 (t, J = 8.6 Hz, 2H), 3.88 (q, J = 7.3 Hz, 1H), 1.62
(d, J = 7.3 Hz, 3H); 13C{1H} NMR (101 MHz, CHLOROFORM-D) δ
162.4 (d, J = 247.2 Hz), 132.9 (d, J = 3.3 Hz), 128.5 (d, J = 8.4 Hz),
121.6, 116.2 (d, J = 21.7 Hz), 30.7, 21.6; 19F NMR (565 MHz,
CHLOROFORM-D) δ -113.81 (s). The spectral data for this
compound match that reported in the literature.5 GC-MS:149
4-(1-Cyanoethyl)benzonitrile (2j): colorless oil, yield: 75%,
35.3 mg; 1H NMR (400 MHz, CHLOROFORM-D) δ 7.68 (d, J = 8.4
Hz, 2H), 7.48 (d, J = 8.3 Hz, 2H), 3.96 (q, J = 7.3 Hz, 1H), 1.65 (d,
J = 7.3 Hz, 3H); 13C{1H} NMR (101 MHz, CHLOROFORM-D) δ
142.2, 133.1, 127.8, 120.4, 118.2, 112.4, 31.4, 21.3. HRMS (ESI)
solid, yield: 83%, 52.5 mg; mp: 71-73 °C; H NMR (400 MHz,
CHLOROFORM-D) δ 7.85 – 7.74 (m, 2H), 7.71 – 7.60 (m, 1H),
7.41 – 7.31 (m, 1H), 7.24 – 7.13 (m, 2H), 4.53 (q, J = 7.2 Hz, 1H),
3.96 (s, 3H), 1.80 (d, J = 7.2 Hz, 3H); 13C{1H} NMR (101 MHz,
CHLOROFORM-D) δ 158.5, 131.2, 130.9, 129.5, 128.8, 125.4,
123.4, 121.8, 118.5, 101.3, 100.0, 55.5, 28.5, 20.1. The spectral
data for this compound match that reported in the literature.5
GC-MS:211
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2-(1-Methyl-1H-indol-3-yl)propanenitrile (2t): white solid,
yield: 83%, 45.9 mg; mp: 62-63 °C; 1H NMR (400 MHz,
CHLOROFORM-D) δ 7.67 – 7.60 (m, 1H), 7.35 – 7.25 (m, 2H),
7.19 – 7.14 (m, 1H), 7.09 – 7.04 (m, 1H), 4.16 (q, J = 7.2 Hz, 1H),
3.77 (s, 3H), 1.74 (d, J = 7.2 Hz, 3H); 13C{1H} NMR (101 MHz,
CHLOROFORM-D) δ 137.4, 126.3, 125.7, 122.4, 122.0, 119.7,
118.6, 110.5, 109.8, 32.9, 22.9, 20.1. The spectral data for this
compound match that reported in the literature.5 GC-MS:184
2-(Benzofuran-3-yl)propanenitrile (2u): colorless oil, yield:
73%, 37.5 mg; 1H NMR (400 MHz, CHLOROFORM-D) δ 7.70 –
7.63 (m, 2H), 7.57 – 7.47 (m, 1H), 7.42 – 7.27 (m, 2H), 4.09 (q,
J = 7.2 Hz, 1H), 1.77 (d, J = 7.3 Hz, 3H); 13C{1H} NMR (101 MHz,
CHLOROFORM-D) δ 155.8, 141.8, 125.4, 125.3, 123.2, 120.5,
119.4, 117.0, 112.1, 21.8, 18.9. The spectral data for this
compound match that reported in the literature.5 GC-MS:171
2-(Benzo[b]thiophen-3-yl)propanenitrile (2v): white solid,
yield: 82%, 46.0 mg; mp: 108-109 °C; 1H NMR (400 MHz,
CHLOROFORM-D) δ 7.99 – 7.84 (m, 1H), 7.84 – 7.73 (m, 1H),
7.53 – 7.32 (m, 3H), 4.24 (q, J = 7.2 Hz, 1H), 1.78 (d, J = 7.0 Hz,
3H); 13C{1H} NMR (101 MHz, CHLOROFORM-D) δ 140.9, 136.4,
130.9, 125.0, 124.7, 123.8, 123.4, 121.2, 120.9, 25.6, 19.2. The
spectral data for this compound match that reported in the
literature.5 GC-MS:187
N, N-Dimethylaniline (2w): colorless oil, yield: 65%, 23.6 mg;
1H NMR (400 MHz, CHLOROFORM-D) δ 7.41 – 7.31 (m, 2H),
6.80 – 6.88 (m, 3H), 3.03 (s, 6H). 13C{1H} NMR (101 MHz,
CHLOROFORM-D) δ 150.8, 129.3, 116.8, 112.8, 40.8. The
spectral data for this compound match that reported in the
literature.10b GC-MS:121
Methyl(p-tolyl)sulfane (2x): colorless oil, yield: 71%, 29.3 mg;
1H NMR (400 MHz, CHLOROFORM-D) δ 7.17 (d, J = 8.2 Hz, 2H),
7.09 (d, J = 7.9 Hz, 2H), 2.45 (s, 3H), 2.30 (s, 3H). 13C{1H} NMR
(101 MHz, CHLOROFORM-D) δ 137.7, 135.9, 129.9, 126.6,
124.7, 20.1, 15.4. The spectral data for this compound match
that reported in the literature.17 GC-MS:138
+
calcd for C10H9N2 [M+H]: 157.0760, found: 157.0761.
2-(4-(Phenylethynyl)phenyl)propanenitrile (2l): white solid,
yield: 71%, 49.2 mg; mp: 105-106 oC 1H NMR (400 MHz,
CHLOROFORM-D) δ 7.55 – 7.51 (m, 4H), 7.35 – 7.32 (m, 5H),
3.91 (q, J = 7.3 Hz, 1H), 1.64 (d, J = 7.3 Hz, 3H); 13C{1H} NMR
(101 MHz, CHLOROFORM-D) δ 137.0, 132.4, 131.7, 128.6,
128.5, 126.9, 123.4, 123.0, 121.3, 90.2, 88.6, 31.2, 21.4. The
spectral data for this compound match that reported in the
literature.5 GC-MS:231
2-(4-(Trimethylsilyl)phenyl)propanenitrile (2m): colorless
oil, yield: 48%, 29.2 mg; 1H NMR (400 MHz, CHLOROFORM-D)
δ 7.54 (d, J = 8.1 Hz, 2H), 7.34 (d, J = 8.0 Hz, 2H), 3.89 (q, J = 7.3
Hz, 1H), 1.64 (d, J = 7.3 Hz, 3H), 0.27 (s, 9H); 13C{1H} NMR
(101 MHz, CHLOROFORM-D) δ 140.7, 137.6, 134.2, 126.1,
100.0, 31.3, 21.4, -1.1. The spectral data for this compound
match that reported in the literature.5 GC-MS:203
2-(o-Tolyl)propanenitrile (2n): colorless oil, yield: 90%, 39.2
mg; 1H NMR (400 MHz, CHLOROFORM-D) δ 7.51 – 7.42 (m, 1H),
7.30 – 7.19 (m, 3H), 4.06 (q, J = 7.2 Hz, 1H), 2.38 (s, 3H), 1.63 (d,
J = 7.2 Hz, 3H); 13C{1H} NMR (101 MHz, CHLOROFORM-D) δ
135.3, 134.8, 131.1, 128.2, 127.1, 126.8, 121.9, 28.2, 20.1, 19.1.
The spectral data for this compound match that reported in the
literature.5 GC-MS:145
2-([1,1'-Biphenyl]-2-yl)propanenitrile (2o): colorless oil, yield:
1
91%, 56.6 mg; H NMR (400 MHz, CHLOROFORM-D) δ 7.69 –
7.61 (m, 1H), 7.49 – 7.34 (m, 5H), 7.31 – 7.23 (m, 3H), 4.03 (q,
J = 7.2 Hz, 1H), 1.49 (d, J = 7.2 Hz, 3H); 13C{1H} NMR (101 MHz,
CHLOROFORM-D) δ 141.1, 140.1, 135.2, 130.6, 129.1, 128.8,
128.6, 128.0, 127.8, 127.2, 122.4, 28.0, 21.5. HRMS (ESI) calcd
for C15H14N+[M+H]: 208.1121, found: 208.1120. GC-MS:174
2-(m-Tolyl)propanenitrile (2p): colorless oil, yield: 84%,
1
36.54 mg; H NMR (400 MHz, CHLOROFORM-D) δ 7.27 – 7.22
(m, 1H), 7.18 – 7.08 (m, 3H), 3.85 (q, J = 7.3 Hz, 1H), 2.36 (s, 3H),
1.62 (d, J = 7.3 Hz, 3H); 13C{1H} NMR (101 MHz, CHLOROFORM-
D) δ 139.1, 137.1, 129.1, 128.8, 127.5, 123.8, 121.8, 31.3, 21.6,
21.5. HRMS (ESI) calcd for C10H12N+[M+H]: 146.0964, found:
146.0964
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2-(Benzo[d][1,3]dioxol-5-yl)propanenitrile (2q): colorless oil,
1
yield: 84%, 44.1 mg; H NMR (400 MHz, CHLOROFORM-D) δ
6.87 – 6.74 (m, 3H), 5.98 (s, 2H), 3.81 (q, J = 7.3 Hz, 1H), 1.61 (d,
J = 7.3 Hz, 3H); 13C{1H} NMR (101 MHz, CHLOROFORM-D) δ
148.4, 147.5, 130.8, 121.7, 120.2, 108.7, 107.3, 101.5, 31.0, 21.6.
The spectral data for this compound match that reported in the
literature.5 GC-MS:175
NMR spectrum for mechanistic study as shown in Figure
S1-S5, and NMR spectra for all products
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