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4.2.18. 1-(4-Ethoxy-3-fluorophenyl)-2-fluoro-2-phenylethan-1-one
(3ja)
4.2.24. 2-Fluoro-1-(4-fluorophenyl)-2-(p-tolyl)ethan-1-one (3fb)
Colorless oil.1H NMR (400 MHz, CDCl3)
8.04–7.89 (m, 2H), 7.35
d
Light yellow oil. 1H NMR (400 MHz, CDCl3)
d
7.80–7.65 (m, 2H),
(dd, J = 8.1,1.5 Hz, 2H), 7.21 (d, J = 8.0 Hz, 2H), 7.13–7.03 (m, 2H), 6.43
7.51–7.44 (m, 2H), 7.44–7.33 (m, 3H), 6.92 (t, J = 8.5 Hz, 1H), 6.42 (d,
(d, J = 48.8 Hz,1H), 2.34 (d, J = 1.7 Hz, 3H). 19F NMR (376 MHz, CDCl3)
J = 48.7 Hz,1H), 4.14 (q, J = 7.0 Hz, 2H),1.46 (t, J = 7.0 Hz, 3H). 19F NMR
d
ꢂ103.35 (s, 1F), ꢂ174.02 (d, J = 49.5 Hz, 1F). 13C NMR (101 MHz,
(376 MHz, CDCl3)
d
ꢂ133.15 (dd, J = 12.4, 9.3 Hz, 1F), ꢂ175.66 (d,
192.05 (d, J = 21.6 Hz),
CDCl3) d 192.89 (d, J = 21.8 Hz), 165.93 (d, J = 256.4 Hz), 139.93,
J = 49.0 Hz, 1F). 13C NMR (101 MHz, CDCl3)
d
131.89 (dd, J = 9.5, 3.0 Hz), 131.15 (d, J = 20.1 Hz), 130.42, 129.88,
127.36, 115.92 (d, J = 21.9 Hz), 94.00 (d, J = 185.8 Hz), 21.28. IR (neat,
cmꢂ1): 3080, 2925, 2854, 1694, 1599, 1507, 1413, 1232, 1156, 1077,
842. MS (EI): m/z (%) 77 (3), 95 (14), 123 (100), 246 (0.97, M+).
HRMS: Calcd. for C15H12F2O: 264.0856; found: 264.0857.
151.93 (d, J = 248.5 Hz), 151.93 (d, J = 11.1 Hz), 134.36 (d, J = 20.0 Hz),
129.63, 129.11, 127.14, 126.76, 116.95, 116.75, 113.19, 94.13 (d,
J = 186.1 Hz), 64.97, 14.54. IR (neat, cmꢂ1): 3068, 2984, 2937, 2924,
1692, 1609, 1517, 1437, 1278, 1143, 1036, 896, 807. MS (EI): m/z (%)
83 (6),111 (11),139 (65),167 (100), 276 (0.35, M+). HRMS: Calcd. for
C
16H14F2O2: 276.0962; found: 276.0964.
4.2.25. 1-(4-(Benzyloxy)phenyl)-2-fluoro-2-(p-tolyl)ethan-1-one
(3hb)
4.2.19. 2-Fluoro-1-(naphthalen-2-yl)-2-phenylethan-1-one (3ka)
Yellow solid. m.p.: 114.3–115.1 ꢁC. 1H NMR (400 MHz, CDCl3)
Yellow solid. m.p.: 85.2–85.8 ꢁC. 1H NMR (400 MHz, CDCl3)
d
d
7.97–7.89 (m, 2H), 7.45–7.34 (m, 7H), 7.20 (d, J = 8.0 Hz, 2H), 7.00–
6.93 (m, 2H), 6.44 (d, J = 48.9 Hz, 1H), 5.09 (s, 2H), 2.34 (d, J = 1.7 Hz,
8.38 (d, J = 8.2 Hz, 1H), 7.98 (d, J = 8.2 Hz, 1H), 7.89–7.78 (m, 2H),
7.59–7.49 (m, 2H), 7.46 (t, J = 7.7 Hz, 3H), 7.40–7.30 (m, 3H), 6.58 (d,
3H). 19F NMR (376 MHz, CDCl3)
NMR (101 MHz, CDCl3) d 192.85, 163.05, 139.65, 135.96, 131.49,
d
ꢂ173.60 (d, J = 48.9 Hz, 1F). 13C
J = 48.4 Hz, 1H). 19F NMR (376 MHz, CDCl3)
d
ꢂ175.87 (d, J = 49.0 Hz,
1F). 13C NMR (101 MHz, CDCl3)
d
197.78 (d, J = 22.4 Hz), 134.06 (d,
129.77, 128.73, 128.33, 127.49, 127.14, 114.74, 93.76 (d, J = 184.6 Hz),
70.18, 21.28. IR (neat, cmꢂ1): 3068, 2923, 2866, 1688, 1598, 1509,
1455,1257, 1172, 1062, 967, 812. MS (EI): m/z (%) 65 (3), 91 (60), 211
(100), 334 (0.1, M+). HRMS: Calcd. for C22H19FO2: 334.1369; found:
334.1366.
J = 20.3 Hz), 133.87, 133.32, 132.59, 130.56, 129.47, 128.98, 128.48,
128.27, 128.13, 127.01, 126.73, 125.25, 124.09, 94.38 (d, J = 188.2 Hz).
IR (neat, cmꢂ1): 3062, 2926, 1695,1592,1456,1237, 1178,1038, 943,
864, 779, 696. MS (EI): m/z (%) 77 (3), 127 (44), 155 (100), 264 (1,
M+). HRMS: Calcd. for C18H13FO: 264.0950; found: 264.0952.
4.2.26. 1-([1,10-Biphenyl]-4-yl)-2-fluoro-2-(p-tolyl)ethan-1-one (3ib)
4.2.20. 2-Fluoro-2-phenyl-1-(thiophen-2-yl)ethanone (3la) [18]
White solid. m.p.: 80.7–81.3 ꢁC. 1H NMR (400 MHz, CDCl3)
d 8.01
1H NMR (400 MHz, CDCl3)
d
7.92 (dt, J = 3.8, 1.1 Hz, 1H), 7.70 (dd,
(d, J = 8.4 Hz, 2H), 7.67–7.61 (m, 2H), 7.58 (dd, J = 5.3, 3.3 Hz, 2H),
7.50–7.43 (m, 2H), 7.40 (d, J = 7.5 Hz, 3H), 7.22 (d, J = 7.9 Hz, 2H), 6.52
(d, J = 48.7 Hz,1H), 2.35 (d, J = 1.7 Hz, 3H). 19F NMR (376 MHz, CDCl3)
J = 4.9, 0.6 Hz, 1H), 7.52 (dd, J = 6.5, 1.4 Hz, 2H), 7.40 (dd, J = 7.2,
3.5 Hz, 3H), 7.13 (dd, J = 4.8, 4.0 Hz, 1H), 6.26 (d, J = 48.4 Hz, 1H). IR
(neat, cmꢂ1): 3063, 2925, 1699, 1472, 1249, 961, 711.
d
ꢂ173.94 (d, J = 48.8 Hz,1F). 13C NMR (101 MHz, CDCl3)
d 193.86 (d,
J = 21.5 Hz), 146.37, 139.86, 139.61, 132.70, 131.37 (d, J = 20.0 Hz),
129.87, 129.67, 128.99, 128.43, 127.60, 127.28, 93.88 (d, J = 185.1 Hz),
21.30. IR (neat, cmꢂ1): 3061, 2928, 2857, 1689, 1590, 1387, 1256,
1164, 971, 833, 698. MS (EI): m/z (%) 119 (1),152 (21),181 (100), 304
(0.1, M+). HRMS: Calcd. for C21H17FO: 304.1263; found: 304.1265.
4.2.21. 2-Fluoro-1,2-di-p-tolylethanone (3bb)
Yellow oil. 1H NMR (400 MHz, CDCl3)
d
7.83 (d, J = 8.2 Hz, 2H),
7.37 (dd, J = 8.0,1.5 Hz, 2H), 7.20 (t, J = 7.0 Hz, 4H), 6.48 (d, J = 48.8 Hz,
1H), 2.37 (s, 3H), 2.33 (s, 3H). 19F NMR (376 MHz, CDCl3)
ꢂ173.88
(d, J = 48.8 Hz, 1F). 13C NMR (101 MHz, CDCl3)
193.86 (d,
d
d
J = 21.2 Hz), 144.73, 139.73, 131.57, 131.40, 129.79, 129.38, 129.15,
127.61, 93.68 (d, J = 184.6 Hz), 21.72, 21.27. IR (neat, cmꢂ1): 3041,
2925, 2853,1693,1607,1411,1265,1182,1063, 967, 814. MS (EI): m/z
(%) 91 (20), 119 (100), 224 (3), 242 (0.56, M+). HRMS: Calcd. for
4.2.27. 2-Fluoro-1-(naphthalen-2-yl)-2-(p-tolyl)ethan-1-one (3kb)
White solid. m.p.: 117.4–118.1 ꢁC. 1H NMR (400 MHz, CDCl3)
d
8.42 (d, J = 8.5 Hz,1H), 7.97 (d, J = 8.3 Hz,1H), 7.88–7.77 (m, 2H), 7.54
(dddd, J = 19.5, 8.0, 6.9, 1.4 Hz, 2H), 7.44 (dd, J = 8.1, 7.4 Hz, 1H), 7.35
(d, J = 6.9 Hz, 2H), 7.15 (d, J = 8.0 Hz, 2H), 6.56 (d, J = 48.4 Hz,1H), 2.30
C16H15FO: 242.1107; found: 242.1108.
(d, J = 1.1 Hz, 3H). 19F NMR (376 MHz, CDCl3)
J = 49.0 Hz, 1F). 13C NMR (101 MHz, CDCl3)
d
d
ꢂ173.88 (d,
4.2.22. 2-Fluoro-1-(4-methoxyphenyl)-2-(p-tolyl)ethan-1-one (3cb)
Yellow oil. 1H NMR (400 MHz, CDCl3)
7.92 (d, J = 5.8 Hz, 2H),
197.81 (d,
d
J = 22.5 Hz), 139.59, 133.89, 133.26, 132.67, 131.09 (d, J = 20.6 Hz),
130.58, 129.72, 128.48, 128.25, 128.12, 127.22, 126.70, 125.33,
124.10, 94.24 (d, J = 187.4 Hz), 21.25. IR (neat, cmꢂ1): 3062, 2958,
2925,1697, 1607, 1265,1185,1066, 974, 813, 765. MS (EI): m/z (%) 77
(2), 127 (36), 155 (100), 260 (6), 278 (0.6, M+). HRMS: Calcd. for
7.37 (d, J = 6.8 Hz, 2H), 7.19 (d, J = 7.9 Hz, 2H), 6.87 (t, J = 5.8 Hz, 2H),
6.45 (d, J = 48.9 Hz, 1H), 3.82 (s, 3H), 2.33 (d, J = 1.4 Hz, 3H). 19F NMR
(376 MHz, CDCl3)
CDCl3)
d
ꢂ173.66 (d, J = 48.9 Hz, 1F). 13C NMR (101 MHz,
d
192.74 (d, J = 21.2 Hz), 163.91, 139.69, 131.70 (d, J = 20.1 Hz),
131.46, 129.79, 127.54, 126.91, 113.93, 93.68 (d, J = 184.4 Hz), 55.50,
21.28. IR (neat, cmꢂ1): 3056, 2961, 2933, 2842, 1689, 1599, 1422,
1262, 1173, 1061, 968, 819. MS (EI): m/z (%) 77 (6), 92 (4), 107 (6),
135 (100), 191 (10), 258 (0.21, M+). HRMS: Calcd. for C16H15FO2:
258.1056; found: 258.1057.
C19H15FO: 278.1107; found: 278.1106.
4.2.28. 2-Fluoro-1-(furan-2-yl)-2-(p-tolyl)ethan-1-one (3mb)
White solid. m.p.: 75.9–76.7 ꢁC. 1H NMR (400 MHz, CDCl3)
d
7.61
(d, J = 1.1 Hz, 1H), 7.43–7.33 (m, 3H), 7.20 (d, J = 8.0 Hz, 2H), 6.54 (dd,
J = 3.6, 1.7 Hz, 1H), 6.27 (d, J = 47.9 Hz, 1H), 2.34 (d, J = 1.5 Hz, 3H). 19
F
4.2.23. 2-Fluoro-1-(o-tolyl)-2-(p-tolyl)ethan-1-one (3db)
NMR (376 MHz, CDCl3)
(101 MHz, CDCl3) d 183.26 (d, J = 24.3 Hz), 149.85, 147.45, 139.75,
d
ꢂ179.08 (d, J = 48.0 Hz, 1F). 13C NMR
Yellow solid. m.p.: 73.2–73.9 ꢁC. 1H NMR (400 MHz, CDCl3)
d
8.04–7.92 (m, 2H), 7.35 (dd, J = 8.1, 1.5 Hz, 2H), 7.21 (d, J = 8.0 Hz, 2H),
131.16 (d, J = 20.5 Hz), 129.62, 127.27, 120.35, 112.55, 93.55 (d,
J = 185.6 Hz), 21.28. IR (neat, cmꢂ1): 3091, 2963, 2923, 1680, 1589,
1441, 1281, 1155, 1065, 801, 765. MS (EI): m/z (%) 77 (5), 91 (26), 105
(8), 119 (100), 123 (20), 218 (5, M+). HRMS: Calcd. for C13H11FO2:
218.0743; found: 218.0742.
7.13–7.03 (m, 2H), 6.43 (d, J = 48.8 Hz,1H), 2.34 (d, J = 1.7 Hz, 3H). 19
F
NMR (376 MHz, CDCl3)
(101 MHz, CDCl3)
d
ꢂ175.57 (d, J = 48.4 Hz, 1F). 13C NMR
d
198.14 (d, J = 22.5 Hz), 139.50, 138.85, 135.02,
131.86, 131.70, 130.93 (d, J = 20.7 Hz), 129.64, 128.36, 127.14, 125.41,
94.20 (d, J = 187.0 Hz), 21.27, 20.61. IR (neat, cmꢂ1): 3061, 2928,
2855, 1598, 1597, 1452, 1226, 10549, 837, 759. MS (EI): m/z (%) 77
(2), 91 (25), 119 (100), 242 (0.41, M+). HRMS: Calcd. for C16H15FO:
242.1107; found: 242.1106.
4.2.29. 2-Fluoro-1,2-di-o-tolylethan-1-one (3dc)
Yellow solid. m.p.: 74.2–74.9 ꢁC. 1H NMR (400 MHz, CDCl3)
d
7.43 (d, J = 7.6 Hz, 1H), 7.37–7.28 (m, 2H), 7.23 (t, J = 3.7 Hz, 1H), 7.17