10.1002/ejoc.201700277
European Journal of Organic Chemistry
p-Methoxyphenylacetonitrile (2a): (commercially available):
4-Biphenylacetonitrile (2j): (commercially available): Yield:
Yield: 191.3 mg (65%); colorless oil; IR (neat): ν
̃
= 1248, 2250
220.7 mg (57%); yellow solid: Mp 93 °C; IR (neat): ν̃
= 2252 cm-1;
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cm-1; H-NMR (400 MHz, CDCl3): δ = 3.69 (s, 2H), 3.81 (s, 3H),
6.90 (d, J = 8.8 Hz, 2H), 7.24 (d, J = 8.6 Hz, 2H) ppm; 13C-NMR
(100 MHz, CDCl3): δ = 22.8, 55.3, 114.5, 118.2, 121.7, 129.0,
159.3 ppm.
1H-NMR (400 MHz, CDCl3): δ = 3.80 (s, 2H), 7.35-7.47 (m, 5H),
7.57-7.62 (m, 4H) ppm; 13C-NMR (100 MHz, CDCl3): δ = 23.3,
117.8, 127.0, 127.6, 127.8, 128.3, 128.8, 128.9, 140.1, 141.1 ppm.
p-Chlorophenylacetonitrile (2k): (commercially available):
o-Methoxyphenylacetonitrile (2b): (commercially available):
Yield: 133.7 mg (44 %); colorless oil; IR (neat): ν̃
= 2251 cm-1; 1H-
Yield: 214.4 mg (73%); white sold: Mp 68 °C; IR (neat): ν
̃
= 1248,
NMR (400 MHz, CDCl3): δ = 3.74 (s, 2H), 7.27 (d, J = 9.1 Hz, 2H),
7.37 (d, J = 9.1 Hz, 2H) ppm; 13C-NMR (100 MHz, CDCl3): δ =
22.9, 117.4, 128.3, 129.2, 133.9 ppm.
2251 cm-1; H-NMR (400 MHz, CDCl3): δ = 3.69 (s, 2H), 3.87 (s,
3H), 6.89 (d, J = 8.4 Hz, 1H), 6.97 (t, J = 7.5 Hz, 1H), 7.30-7.37
(m, 2H) ppm; 13C-NMR (100 MHz, CDCl3): δ = 18.6, 55.4, 110.4,
118.0, 118.5, 120.7, 129.1, 129.5, 156.7 ppm.
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p-Bromophenylacetonitrile (2l): (commercially available): Yield:
216.8 mg (55%); white solid: Mp 49 °C; IR (neat): ν̃
= 2249 cm-1;
Phenylacetonitrile (2c): (commercially available): Yield: 144.1
1H-NMR (400 MHz, CDCl3): δ = 3.71 (s, 2H), 7.22 (d, J = 8.5 Hz,
2H), 7.52 (d, J = 8.4 Hz, 2H) ppm; 13C-NMR (100 MHz, CDCl3):
δ = 23.2, 117.3, 122.1, 128.8, 129.6, 132.3 ppm.
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mg (62%); colorless oil; IR (neat): ν
̃
= 2251 cm-1; H-NMR (400
MHz, CDCl3): δ = 3.76 (s, 2H), 7.32-7.41 (m, 5H) ppm; 13C-NMR
(100 MHz, CDCl3): δ = 23.5, 117.8, 127.8, 127.9, 129.0, 129.8
ppm.
2-Naphthylacetonitrile (2m): (commercially available): Yield:
177.2 mg (53%); yellow solid: Mp 84 °C; IR (neat): ν̃
= 2251 cm-1;
p-Methylphenylacetonitrile (2d): (commercially available):
1H-NMR (400 MHz, CDCl3): δ = 3.93 (s, 2H), 7.39 (dd, J = 8.6,
1.8 Hz, 1H), 7.49-4.55 (m, 2H), 7.83-7.88 (m, 4H) ppm; 13C-NMR
(100 MHz, CDCl3): δ = 23.8, 117.8, 125.4, 126.5, 126.7, 126.8,
127.2, 127.6, 127.7, 129.0, 132.7, 133.3 ppm.
Yield: 160.6 mg (61%); colorless oil; IR (neat): ν̃
= 2250 cm-1; 1H-
NMR (400 MHz, CDCl3): δ = 2.35 (s, 2H), 3.71 (s, 2H), 7.17-7.22
(m, 4H) ppm; 13C-NMR (100 MHz, CDCl3): δ = 21.0, 23.1, 118.0,
126.7, 127.7, 129.7, 137.7 ppm.
1-Naphthylacetonitrile (2n): Yield: 247.8 mg (74%); colorless
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m-Methylphenylacetonitrile (2e): (commercially available):
oil; IR (neat): ν
̃
= 2252 cm-1; H-NMR (400 MHz, CDCl3): δ =
Yield: 184.4 mg (70%); colorless oil; IR (neat): ν
̃
= 2250 cm-1; 1H-
4.15 (s, 2H), 7.46-7.50 (m, 1H), 7.55-7.64 (m, 3H), 7.87 (d, J = 8.1,
1H), 7.88 (d, J = 8.5 Hz, 1H), 7.92 (d, J = 7.6 Hz, 1H) ppm; 13C-
NMR (100 MHz, CDCl3): δ = 21.6, 117.7, 122.3, 125.4, 125.7,
126.3, 126.4, 127.0, 129.0, 129.1, 130.7, 133.6 ppm; HRMS (ESI):
calcd. for C12H8N [M-H]+ 166.0651, found 166.0656.
NMR (400 MHz, CDCl3): δ = 2.36 (s, 3H), 3.71 (s, 2H), 7.11-7.15
(m, 3H), 7.26 (t, J = 7.6 Hz, 1H) ppm; 13C-NMR (100 MHz,
CDCl3): δ = 21.3, 23.5, 118.0, 124.9, 128.6, 128.7, 129.0, 129.7,
139.0 ppm.
o-Methylphenylacetonitrile (2f): (commercially available): Yield:
p-Allyloxyphenylacetonitrile (2o): Yield: 184.3 mg (53%);
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198.9 mg (76%); colorless oil; IR (neat): ν
̃
= 2250 cm-1; 1H-NMR
colorless oil; IR (neat): ν
̃
= 1244, 1612, 2250 cm-1; H-NMR (400
(400 MHz, CDCl3): δ = 2.35 (s, 3H), 3.67 (s, 2H), 7.20-7.28 (m,
3H), 7.36 (d, J = 7.7 Hz, 1H) ppm; 13C-NMR (100 MHz, CDCl3): δ
= 19.1, 21.7, 117.5, 126.6, 128.2, 128.3, 128.4, 130.5, 135.9 ppm.
MHz, CDCl3): δ = 3.68 (s, 2H), 4.54 (dt, J = 5.2, 1.6 Hz, 2H), 5.30
(dq, J = 10.4, 1.4 Hz, 1H), 5.42 (dq, J = 17.2, 1.6 Hz, 1H), 6.00-
610 (m, 1H), 6.91 (d, J = 8.6 Hz, 2H) 7.23 (d, J = 8.8 Hz, 2H)
ppm; 13C-NMR (100 MHz, CDCl3): δ = 22.7, 68.8, 115.2, 117.8,
118.2, 121.8, 129.0, 132.9, 158.2 ppm; HRMS (APCI): calcd. for
C11H11ON [M]+ 173.0835, found 173.0833.
o-Ethylphenylacetonitrile (2g): Yield: 199.5 mg (69%); colorless
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oil; IR (neat): ν
̃
= 2249 cm-1; H-NMR (400 MHz, CDCl3): δ =
1.26 (t, J = 7.5 Hz, 3H), 2.67 (q, J = 7.5Hz, 2H), 3.71 (s, 2H), 7.21-
7.26 (m, 2H), 7.29-7.33 (m, 1H), 7.38 (d, J = 7.7 Hz, 1H) ppm;
13C-NMR (100 MHz, CDCl3): δ = 14.3, 21.3, 25.6, 117.9, 126.6,
127.7, 128.6, 128.7, 128.8, 141.7 ppm; HRMS (APCI): calcd. for
C10H12N [M+H]+ 146.0964, found 146.0963.
1-Tosylindole-3-acetonitrile (2p): Yield: 254.5 mg (41%); white
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solid: Mp 160 °C; IR (neat): ν
̃
= 2258 cm-1; H-NMR (400 MHz,
CDCl3): δ = 2.35 (s, 3H), 3.76 (s, 2H), 7.25 (d, J = 8.5 Hz, 2H),
7.30 (t, J = 7.8 Hz, 1H), 7.39 (t, J = 7.4 Hz, 1H), 7.50 (d, J = 7.5
Hz, 1H), 7.62 (s, 1H), 7.79 (d, J = 8.5 Hz, 2H), 8.02 (d, J = 8.3 Hz,
1H) ppm; 13C-NMR (100 MHz, CDCl3): δ = 14.4, 21.6, 111.3,
113.9, 116.7, 118.8, 123.6, 124.4, 125.5, 126.9, 128.7, 130.0, 134.9,
135.1, 145.3 ppm; HRMS (ESI): calcd. for C17H14O2N2SNa
[M+Na]+ 333.0668, found 333.0666.
3,5-Dimethylphenylacetonitrile (2h): Yield: 174.4 mg (60%);
colorless oil; IR (neat): ν̃
= 2249 cm-1; 1H-NMR (400 MHz,
CDCl3): δ = 2.32 (s, 6H), 3.67 (s, 2H), 6.94 (s, 2H), 6.96 (s, 1H)
ppm; 13C-NMR (100 MHz, CDCl3): δ = 21.1, 23.3, 118.1, 125.6,
129.5, 129.6, 138.7 ppm; HRMS (APCI): calcd. for C10H12N
[M+H]+ 146.0964, found 146.0968.
Benzo[b]thiophen-3-acetonitrile (2q): Yield: 184.7 mg (53%);
white solid: Mp 65 °C; IR (neat): ν̃
= 2253 cm-1; 1H-NMR (400
Mesitylacetonitrile (2i): (commercially available): Yield: 212.0
MHz, CDCl3): δ = 3.92 (s, 2H), 7.43 (td, J = 7.3, 1.6 Hz, 1H), 7.46
(td, J = 7.0, 1.4 Hz, 1H), 7.50 (s, 1H), 7.70-7.72 (m, 1H), 7.89-7.91
(m, 1H) ppm; 13C-NMR (100 MHz, CDCl3): δ = 17.7, 116.9, 120.1,
123.1, 123.8, 124.6, 124.9, 125.0, 136.9, 140.4 ppm; HRMS
(APCI): calcd. for C10H7NS [M]+ 173.0294, found 173.0293.
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mg (67%); white solid: Mp 79 °C; IR (neat): ν
̃
= 2243 cm-1; H-
NMR (400 MHz, CDCl3): δ = 2.27 (s, 3H), 2.36 (s, 6H), 3.61 (s,
2H), 6.90 (s, 2H) ppm; 13C-NMR (100 MHz, CDCl3): δ = 17.3,
19.9, 20.8, 117.4, 124.3, 129.3, 136.4, 137.8 ppm.
Submitted to the European Journal of Organic Chemistry
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