E
X. Zheng et al.
Paper
Synthesis
1H NMR (400 MHz, CDCl3): δ = 7.57 (d, J = 7.7 Hz, 2 H), 7.50 (d, J = 7.5
Hz, 2 H), 7.40 (t, J = 7.5 Hz, 2 H), 7.31 (d, J = 7.2 Hz, 1 H), 7.23 (d, J = 7.6
Hz, 2 H), 2.62 (t, J = 7.6 Hz, 2 H), 1.67 (dd, J = 14.8, 7.4 Hz, 2 H), 0.97 (t,
J = 7.3 Hz, 3 H).
White solid; yield: 129 mg (72%); mp 90–92 °C; Rf = 0.3 (EtOAc/hex-
ane, 1:10).
1H NMR (400 MHz, CDCl3): δ = 7.72 (q, J = 8.2 Hz, 2 H), 7.68 (d, J = 8.4
Hz, 2 H), 7.59 (d, J = 7.4 Hz, 2 H), 7.49 (t, J = 7.3 Hz, 2 H), 7.44 (d, J = 7.2
Hz, 1 H).
13C NMR (101 MHz, CDCl3): δ = 141.87, 141.26, 138.65, 128.92,
128.73, 127.03, 127.01, 126.99, 37.75, 24.57, 13.91.
MS (EI): m/z = 196 [M+].
13C NMR (101 MHz, CDCl3): δ = 145.67, 139.18, 132.59, 129.12,
128.67, 127.73, 127.23, 118.92, 110.94.
MS (EI): m/z = 179 [M+].
4-Benzyl-1,1′-biphenyl (8)
The spectroscopic data are in accordance with those reported.7
4-Chloro-1,1′-biphenyl (13)
Yellow solid; yield: 178 mg (73%); mp 86–88 °C; Rf = 0.55 (hexane).
The spectroscopic data are in accordance with those reported.7
1H NMR (400 MHz, CDCl3): δ = 7.56 (dd, J = 8.3, 0.9 Hz, 2 H), 7.53–7.48
(m, 2 H), 7.40 (t, J = 7.6 Hz, 2 H), 7.34–7.25 (m, 4 H), 7.25–7.19 (m, 4
H), 4.01 (s, 2 H).
13C NMR (101 MHz, CDCl3): δ = 141.04, 140.28, 139.09, 129.35,
128.99, 128.74, 128.54, 127.28, 127.24, 127.10, 127.03, 126.17, 41.63.
Colorless oil; yield: 150 mg (80%); Rf = 0.45 (EtOAc/hexane, 1:100).
1H NMR (400 MHz, CDCl3): δ = 7.55 (d, J = 7.7 Hz, 2 H), 7.52 (d, J = 8.1
Hz, 2 H), 7.43 (dd, J = 18.1, 7.9 Hz, 4 H), 7.37 (d, J = 7.5 Hz, 1 H).
13C NMR (101 MHz, CDCl3): δ = 140.01, 139.68, 133.39, 128.92,
128.90, 128.41, 127.61, 127.01.
MS (EI): m/z = 244 [M+].
MS (EI): m/z = 188 [M+].
1-([1,1′-Biphenyl]-4-yl)ethanone (9)
The spectroscopic data are in accordance with those reported.14
3-Chloro-1,1′-biphenyl (14)
The spectroscopic data are in accordance with those reported.15
Colorless oil; yield: 127 mg (65%); mp 153–155 °C; Rf = 0.45 (EtO-
Ac/hexane, 1:100).
1H NMR (400 MHz, CDCl3): δ = 8.04 (d, J = 8.5 Hz, 2 H), 7.69 (d, J = 8.5
Hz, 2 H), 7.65–7.61 (m, 2 H), 7.47 (t, J = 7.4 Hz, 2 H), 7.40 (t, J = 7.3 Hz,
1 H), 2.64 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 197.70, 145.79, 139.89, 135.90,
128.95, 128.90, 128.22, 127.26, 127.22, 26.63.
MS (EI): m/z = 196 [M+].
White solid; yield: 141 mg (75%); mp 86–88 °C; Rf = 0.45 (EtOAc/hex-
ane, 1:100).
1H NMR (400 MHz, CDCl3): δ = 7.61–7.55 (m, 3 H), 7.47 (ddd, J = 9.8,
6.8, 5.1 Hz, 3 H), 7.42–7.31 (m, 3 H).
13C NMR (101 MHz, CDCl3): δ = 143.12, 139.85, 134.69, 129.99,
128.91, 127.88, 127.33, 127.28, 127.13, 125.31.
MS (EI): m/z = 188 [M+].
2-Chloro-1,1′-biphenyl (15)
The spectroscopic data are in accordance with those reported.16
4-Fluoro-1,1′-biphenyl (10)
The spectroscopic data are in accordance with those reported.7
Colorless oil; yield: 196 mg (51%); Rf = 0.45 (EtOAc/hexane, 1:100).
White solid; yield: 117 mg (68%); mp 76–78 °C; Rf = 0.45 (EtOAc/hex-
ane, 1:100).
1H NMR (400 MHz, CDCl3): δ = 7.48 (d, J = 7.8 Hz, 1 H), 7.45 (d, J = 4.1
Hz, 4 H), 7.40 (dd, J = 5.8, 2.7 Hz, 1 H), 7.37–7.34 (m, 1 H), 7.34–7.28
(m, 2 H).
13C NMR (101 MHz, CDCl3): δ = 163.99, 140.55, 139.44, 132.53,
131.42, 129.97, 129.48, 128.57, 128.08, 127.64, 126.86.
1H NMR (400 MHz, CDCl3): δ = 7.56 (d, J = 7.1 Hz, 4 H), 7.45 (t, J = 7.4
Hz, 2 H), 7.37 (d, J = 7.1 Hz, 1 H), 7.14 (t, J = 8.3 Hz, 2 H).
13C NMR (101 MHz, CDCl3): δ = 163.72, 161.27, 140.28, 137.37 (d, J =
3.1 Hz), 128.82, 128.69 (d, J = 8.1 Hz, 1 H), 127.26, 127.03, 115.61 (d,
J = 21.4 Hz, 1 H).
MS (EI): m/z = 188 [M+].
MS (EI): m/z = 172 [M+].
2-Phenylthiophene (16)
The spectroscopic data are in accordance with those reported.17
2-Fluoro-1,1′-biphenyl (11)
The spectroscopic data are in accordance with those reported.15
Colorless oil; yield: 86 mg (54%); Rf = 0.45 (EtOAc/hexane, 1:100).
1H NMR (400 MHz, CDCl3): δ = 7.63 (d, J = 7.7 Hz, 2 H), 7.37 (t, J = 7.2
Hz, 2 H), 7.34–7.23 (m, 3 H), 7.13–7.06 (m, 1 H).
13C NMR (101 MHz, CDCl3): δ = 144.42, 134.43, 128.88, 128.00,
127.46, 125.97, 124.80, 123.08.
MS (EI): m/z = 160 [M+].
White solid; yield: 89 mg (52%); mp 71–73 °C; Rf = 0.45 (EtOAc/hex-
ane, 1:100).
1H NMR (400 MHz, CDCl3): δ = 7.55 (d, J = 7.6 Hz, 2 H), 7.43 (t, J = 7.5
Hz, 3 H), 7.37 (d, J = 7.3 Hz, 1 H), 7.30 (d, J = 6.9 Hz, 1 H), 7.20 (dd, J =
13.6, 6.1 Hz, 1 H), 7.17–7.10 (m, 1 H).
13C NMR (101 MHz, CDCl3): δ = 161.03, 158.57, 135.85, 130.79 (d, J =
3.4 Hz), 129.01 (dd, J = 9.7, 5.5 Hz), 128.44, 127.66, 124.34 (d, J = 3.7
Hz), 116.21, 115.99.
3-Phenylpyridine (17)
The spectroscopic data are in accordance with those reported.18
MS (EI): m/z = 172 [M+].
Colorless oil; yield: 105 mg (68%); Rf = 0.55 (EtOAc/hexane, 1:100).
1H NMR (400 MHz, CDCl3): δ = 8.85 (s, 1 H), 8.59 (d, J = 3.6 Hz, 1 H),
7.86 (d, J = 7.8 Hz, 1 H), 7.58 (d, J = 7.0 Hz, 2 H), 7.47 (t, J = 7.1 Hz, 2 H),
7.41 (d, J = 6.8 Hz, 1 H), 7.38–7.33 (m, 1 H).
4-Cyano-1,1′-biphenyl (12)
The spectroscopic data are in accordance with those reported.7
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2018, 50, A–G