The Journal of Organic Chemistry
Page 12 of 16
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(99.4 mg, 55%): 1H NMR δ 2.63 (s,3H), 3.87 (s,3H), 6.94 (d, J = 8.2 Hz, 1H), 7.12-7.18 (m,1H),
7.21 (d, J = 7.4 Hz, 1H), 7.38 (t, J = 7.9 Hz, 1H), 7.67 (d, J = 8.5 Hz, 2H),8.02 (d, J = 8.5 Hz,
2H); 13C NMR, δ 26.64, 55.4, 113.1, 113.6, 119.8, 127.3, 128.9, 130.0, 136.0, 141.4, 145.7, 160.1,
197.7. GC-MS (tR 12.2 min) m/z 226 (56, M+). HRMS [M+H]+ for C15H15O2, calcd: 227.1067;
found: 227.1069.
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3-Methoxyl-3'-methylbiphenyl (11j). Treatment of 8 (109.4 mg, 0.20 mmol) with
3-iodo-1-methylbenzene 5j (102.7 µL, 174.4 mg, 0.8 mmol) by Typical Procedure gave 11j56
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(53.9 mg, 34%): H NMR δ 2.44 (s, 3H),3.88 (s,3H), 6.90-6.92 (m, 1H), 7.13-7.16 (m, 1H),
7.17-7.22 (m,2H), 7.33-7.38 (m,2H), 7.42 (d, J = 8.1 Hz, 2H); 13C NMR, δ 20.5, 54.3, 111.6,
111.9, 118.7, 123.3, 127.0, 127.1, 127.6, 128.6, 137.3, 140.1, 141.9. GC-MS (tR 9.6 min) m/z 198
(100, M+). HRMS [M+H]+ for C14H15O, calcd: 199.1117; found: 199.1121.
4'-Acetyl-4-chlorobiphenyl (12b). Treatment of tetra-(p-chlorophenyl)tin 9 (113 mg, 0.20
mmol) with 4-iodoacetophenone 5b (196.8 mg, 0.8 mmol) by Typical Procedure gave 12b55
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(119.6 mg, 65%): H NMR δ 2.62 (s, 3H), 7.42 (d, J = 8.6Hz, 2H), 7.54 (d, J = 8.6 Hz, 2H),
7.63(d, J = 8.6Hz, 2H), 8.02 (d, J = 8.6 Hz, 2H); 13C NMR δ 25.6, 126.0, 127.5, 128.0, 128.1,
133.4, 135.1, 137.3, 143.4, 196.5. GC-MS (tR 11.8 min) m/z 230 (50, M+). HRMS [M+H]+ for
C14H12ClO, calcd: 231.0571; found: 231.0572.
4-Methoxyl-4'-chlorobiphenyl (12d). Treatment of 9 (113 mg, 0.20 mmol) with
4-iodo-1-methoxylbenzene 5d (187.2 mg, 0.8 mmol) by Typical Procedure gave 12d57 (73.2 mg,
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42%): H NMR δ 3.84 (s, 3H), 6.96 (d, J = 8.8Hz, 2H), 7.38 (d, J = 8.6 Hz, 2H), 7.44-7.50 (m,
4H); 13C NMR δ 55.4, 114.4, 128.0, 128.0, 128.9, 132.5, 132.7, 139.3, 159.4. GC-MS (tR 10.6
min) m/z 218 (100, M+). HRMS [M+H]+ for C13H12ClO, calcd: 219.0571; found: 219.0571.
4-Chloro-2'-(trifluoromethyl)biphenyl (12f). Treatment of 9 (113 mg, 0.20 mmol) with
2-iodo-1-(trifluoromethyl)benzene 5f (112.2 µL, 217.6 mg, 0.8 mmol) by Typical Procedure gave
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12f (167.9 mg, 82%): H NMR δ 7.27 (d, J = 4.7Hz, 2H), 7.31 (d, J = 5.1 Hz, 1H), 7.38 (d, J =
5.6 Hz, 2H), 7.49 (t, J = 4.8 Hz, 1H), 7.57 (t, J = 5.0 Hz, 1H), 7.75 (d, J = 5.3 Hz, 1H); 13C NMR
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δ 131.2 (q, J = 272 Hz), 125.2 (q, J = 5.0 Hz), 126.7, 127.0, 127.3 (q, J = 31.3 Hz), 129.3,
130.4, 130.9, 132.8, 137.2, 139.1. GC-MS (tR 7.5 min) m/z 256 (100, M+). HRMS [M+H]+ for
C13H9ClF3, calcd: 257.0339; found: 257.0343.
4-Chloro-3'-cyanobiphenyl (12h). Treatment of 9 (113 mg, 0.20 mmol) with
1-cyano-3-iodobenzene 5h (183.2 mg, 0.8 mmol) by Typical Procedure gave 12h58 (134.6 mg,
79%): 1H NMR δ 7.44-7.50 (m, 4H), 7.52-7.57 (m, 1H), 7.60-7.67 (m, 1H), 7.76 (s, 1H), 7.82 (s,
1H);13C NMR δ 113.2, 118.6, 128.3, 129.3, 129.8, 130.5, 131.0, 131.3, 134.7, 137.3, 141.2.
GC-MS (tR 11.0 min) m/z 213 (100, M+). HRMS [M+H]+ for C13H9ClN, calcd: 214.0418; found:
214.0421.
4-Chloro-3'-methylbiphenyl (12j). Treatment of 9 (113 mg, 0.20 mmol) with
3-iodo-1-methylbenzene 5j (102.7 µL, 174.4 mg, 0.8 mmol) by Typical Procedure gave 12j59
(61.4 mg, 38%): 1H NMR δ 2.44 (s, 3H), 7.20 (d, J = 4.7 Hz, 1H), 7.33-7.39 (m, 3H), 7.41 (d, J =
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4.7 Hz, 2H), 7.52 (d, J=5.3 Hz, 2H); C NMR δ 20.5, 126.7, 127.3, 127.4, 127.8, 127.8, 132.2,
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