JOURNAL OF BIOMOLECULAR STRUCTURE AND DYNAMICS
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25.3, 8.8 Hz), 113.1 (dd, C-17, JCF ¼ 24.0, 8.6 Hz), 110.9, 90.3, 5.3 Hz), 116.7 (dd, C-13, JCF ¼ 25.2, 8.6 Hz), 113.6 (dd, C-15,
55.6, 55.3, 28.9, 28.5, 22.3; IR (KBr, cmꢁ1) Vmax 2939, 1611,
1596, 1496, 1457, 1205, 1153, 1121; Anal. calcd for
JCF ¼ 23.9, 8.5 Hz), 103.9, 98.7, 55.5, 55.4, 30.1, 29.5, 28.8; IR
(KBr, cmꢁ1) Vmax 2936, 1613, 1495, 1464, 1208; Anal. calcd
C18H20F2O3: C. 67.07; H: 6.25; Found: C: 66.72; H: 6.22.
for C17H18F2O2: C: 69.85; H: 6.21; Found: C: 69.59; H: 6.29.
2-(3-(2,5-Difluoro-4-methoxyphenyl)propyl)-1,3,5-trime-
thoxybenzene (19)
1-Fluoro-2-(3-(4-methoxyphenyl)propyl)benzene (31)
Colorless liquid; yield 47%; Rf ¼ (EtOAc/Hexanes 20:80) ¼
0.93; 1H NMR (400 MHz, CDCl3) d 7.22 ꢁ 7.13 (m, 4H),
7.11 ꢁ 7.02 (m, 2H), 6.89 ꢁ 6.86 (m, 2H), 3.82 (s, 3H), 2.72 (t,
2H, J ¼ 7.6 Hz), 2.66 (t, 2H, J ¼ 8 Hz), 1.96 (tt, 2H, J ¼ 15.2,
White solid; yield 80%; Rf ¼ (EtOAc/Hexanes 30:70) ¼ 0.83;
m.p. 80-82 ꢀC; 1H NMR (400 MHz, CDCl3) d 6.98 ꢁ 6.93 (m,
1H). 6.66 ꢁ 6.61 (m, 1H), 6.13 (s, 2H), 3.84 (s, 3H), 3.80 (s, 3H),
3.79 (s, 6H), 2.63 ꢁ 2.55 (m, 4H), 1.74 (tt, 2H, J ¼ 15.6, 8.0 Hz);
13C NMR (100 MHz, CDCl3) d 159.4, 159.0 (C-4/C-6), 156.8 (dd,
C-15, JCF ¼ 239.2, 2.3 Hz), 148.6 (dd, C-12, JCF ¼ 239.1,
8.8 Hz); 13C NMR (100 MHz, CDCl3) d 161.4 (d, C-14, JCF
¼
243.3 Hz), 158.0, 134.4, 130.6 (d, C-11, JCF ¼ 5.3 Hz), 129.6 (C-
4/C-6), 129.4 (d, C-10, JCF ¼ 15.7 Hz), 127.7 (d, C-15, JCF
7.9 Hz), 124.1 (d, C-12, JCF ¼ 3.6 Hz), 115.4 (d, C-13, JCF
¼
¼
2.7 Hz), 145.9 (d, C-13, JCF ¼ 22.6 Hz), 121.6 (dd, C-10, JCF
¼
21.9 Hz), 113.9 (C-1/C-3), 55.5, 34.9, 32.2, 28.9; IR (KBr, cmꢁ1
)
18.7, 6.0 Hz), 116.9 (dd, C-11, JCF ¼ 20.1, 7.0 Hz), 111.3, 101.6
(d, C-14, JCF ¼ 28.9 Hz), 90.8 (C-1/C-3), 56.7, 55.8, 55.5, 29.4,
27.9, 22.3; IR (KBr, cmꢁ1) Vmax 2939, 1609, 1596, 1519, 1455,
1332, 1151; Anal. calcd for C19H22F2O4: C. 64.76; H. 6.29;
Found: C: 64.65; H: 6.00.
Vmax 2934, 2860, 2061, 1879, 1612, 1512; Anal. calcd for
C16H17FO: C: 78.66; H: 7.01; Found: C: 78.53; H: 7.10.
3-(4-Fluorophenyl)-1-(4-methoxyphenyl)propan-1-ol (32)
Light yellow liquid; yield 44%; Rf ¼ (EtOAc/Hexanes 20:80) ¼
0.33; 1H NMR (400 MHz, CDCl3) d 7.26 (d, 2H, J ¼ 8.8 Hz),
7.14 ꢁ 7.11 (m, 2H), 6.99 ꢁ 6.94 (m, 2H), 6.89 (d, 2H,
J ¼ 8.8 Hz), 4.62 ꢁ 4.58 (m, 1H), 3.80 (s, 3H), 2.73 ꢁ 2.57 (m,
2H), 2.14 ꢁ 2.10 (m, 1H), 2.03 (s, 1H, C-OH), 2.0 ꢁ 1.91 (m, 1H);
13C NMR (100 MHz, CDCl3) d 161.5 (d, C-15, JCF ¼ 242.2 Hz),
159.3, 137.6 (d, C-10, JCF ¼ 3.3 Hz), 136.8, 129.9 (d, C-11/C-14,
1-(3-(2-Fluorophenyl)propyl)-2,4-dimethoxybenzene (28)
Light yellow liquid; yield 45%; Rf ¼ (EtOAc/Hexanes 10:90) ¼
0.93; 1H NMR (400 MHz, CDCl3) d 7.26 ꢁ 7.15 (m, 2H).
7.10 ꢁ 7.00 (m, 3H), 6.48 (d, 1H, J ¼ 2.4 Hz), 6.45 (dd, 1H,
J ¼ 8.0, 2.4 Hz), 3.82 (s, 6H), 2.77 (t, 2H, J ¼ 8.0 Hz), 2.65 (t, 2H,
J ¼ 7.6 Hz), 1.92 (tt, 2H, J ¼ 15.6, 8.0 Hz); 13C NMR (100 MHz,
CDCl3) d 161.4 (d, C-14, JCF ¼ 243.2 Hz), 159.3, 158.6, 130.8
(d, C-11, JCF ¼ 5.1 Hz), 130.15, 129.7 (d, C-10, JCF ¼ 15.7 Hz),
127.5 (d, C-15, JCF ¼ 8.1 Hz), 124.0 (d, C-12, JCF ¼ 3.4 Hz),
123.2, 115.3 (d, C-13, JCF ¼ 22.3 Hz), 103.9, 98.7, 55.6, 55.5,
30.5, 29.6, 29.0; IR (KBr, cmꢁ1) Vmax 2936, 2861, 2071, 1613,
1587, 1505; Anal. calcd for C17H19FO2: C: 74.43; H: 6.98;
Found: C: 74.14; H: 7.24.
JCF ¼ 7.6 Hz), 127.4 (C-4/C-6), 115.2 (d, C-13/C-12, JCF
¼
20.8 Hz), 114.2 (C-1/C-3), 73.6, 55.5, 40.7, 31.4; IR (KBr, cmꢁ1
)
Vmax 3387, 2933, 1709, 1610, 1509; Anal. calcd for
C16H17FO2: C: 73.83; H: 6.58; Found: C: 73.67; H: 6.71.
1,4-Difluoro-2-(3-(4-methoxyphenyl)propyl)benzene (33)
Colorless liquid; yield 73%; Rf ¼ (EtOAc/Hexanes 20:80) ¼
0.93; 1H NMR (400 MHz, CDCl3) d 7.13 (d, 2H, J ¼ 8.4 Hz),
6.99 ꢁ 6.93 (m, 1H), 6.91 ꢁ 6.82 (m, 4H), 3.81 (s, 3H),
2.68 ꢁ 2.61 (m, 4H), 1.93 (tt, 2H, J ¼ 15.2, 7.6 Hz); 13C NMR
(100 MHz, CDCl3) d 158. 8 (dd, C-12, JCF ¼ 242.3, 2.3 Hz),
158.1, 157.3 (dd, C-14, JCF ¼ 239.1, 2.5 Hz), 134.1, 131.1 (dd,
C-10, JCF ¼ 18.7, 7.7 Hz), 129.6 (C-4/C-6), 116.9 (dd, C-11, JCF
¼ 23.3, 5.3 Hz), 116.2 (dd, C-13, JCF ¼ 25.4, 8.9 Hz), 114.0 (C-
1/C-3), 113.8 (dd, C-15, JCF ¼ 24.1, 8.7 Hz), 55.5, 34.7, 31.8,
28.8; IR (KBr, cmꢁ1) Vmax 2935, 2861, 1612, 1513, 1495, 1246;
Anal. calcd for C16H16F2O: C: 73.27; H: 6.15; Found: C: 73.31;
H: 6.28.
1-(3-(4-Fluorophenyl)propyl)-2,4-dimethoxybenzene (29)
Yellow liquid; yield 57%; Rf ¼ (EtOAc/Hexanes 10:90) ¼ 0.83;
1H NMR (400 MHz, CDCl3) d 7.18 ꢁ 7.15 (m, 2H), 7.05 ꢁ 6.96
(m, 3H), 6.47 ꢁ 6.44 (m, 2H), 3.81 (m, 6H), 2.67 ꢁ 2.59 (m, 4H),
1.89 (tt, 2H, J ¼ 15.6, 8.0. Hz); 13C NMR (100 MHz, CDCl3) d
161.4 (d, C-15, JCF ¼ 241.3 Hz), 159.4, 158.6, 138.5 (d, C-10,
JCF ¼ 3.0 Hz), 130.2, 129.9 (d, C-11/C-14, JCF ¼ 7.7 Hz), 123.2,
115.0 (d, C-13/C-12, JCF ¼ 20.9 Hz), 103.9, 98.7, 55.6, 55.5,
35.1, 31.9, 29.5; IR (KBr, cmꢁ1) Vmax 2935, 2858, 1613, 1508,
1208; Anal. calcd for C17H19FO2: C: 74.43; H: 6.98; Found: C:
74.25; H: 6.92.
4-(3-(2-Fluorophenyl)propyl)phenol (71)
1-(3-(2,5-Difluorophenyl)propyl)-2,4-dimethoxyben-
zene (30)
Light yellow liquid; yield 50%; Rf ¼ (EtOAc/Hexanes 20:80) ¼
0.56; 1H NMR (400 MHz, CDCl3) d 7.20 ꢁ 7.15 (m, 2H),
7.08 ꢁ 6.99 (m, 4H), 6.77 (d, 2H, J ¼ 8.4 Hz), 4.96 (bs, 1H), 2.68
(t, 2H, J ¼ 7.6 Hz), 2.61 (t, 2H, J ¼ 7.6 Hz), 1.92 (tt, 2H, J ¼ 15.6,
Colorless liquid; yield 78%; Rf ¼ (EtOAc/Hexanes 20:80) ¼
0.83; 1H NMR (400 MHz, CDCl3) d 7.03 (d, 1H, J ¼ 8.4 Hz),
6.98 ꢁ 6.89 (m, 2H), 6.86 ꢁ 6.80 (m, 1H), 6.46 (d, 1H,
J ¼ 2.4 Hz), 6.43 (dd, 1H, J ¼ 8.0, 2.4 Hz), 3.80 (s, 6H),
2.68 ꢁ 2.59 (m, 4H), 1.88 (tt, 2H, J ¼ 15.6, 8.0 Hz); 13C NMR
(100 MHz, CDCl3) d 159.4, 158.5, 158.8 (dd, C-12, JCF ¼ 237.7,
2.3 Hz), 157.3 (dd, C-14, JCF ¼ 239.2, 2.4 Hz), 131.4 (dd, C-10,
8.0 Hz); 13C NMR (100 MHz, CDCl3) d 161.4 (d, C-16, JCF
¼
243 Hz), 153.7, 134.6, 130.8 (d, C-12, JCF ¼ 20.8 Hz), 129.7 (C-
4/C-6), 129.3 (d, C-11, JCF ¼ 15.8 Hz), 127.6 (d, C-14, JCF
8 Hz), 124.1 (d, C-13, JCF ¼ 3.5 Hz), 115.4 (d, C-15, JCF
¼
¼
JCF ¼ 18.7, 7.5 Hz), 130.2, 122.9, 116.8 (dd, C-11, JCF ¼ 23.3, 22.1 Hz), 115.3 (C-3/C-1), 34.8, 32.2, 28.8; IR (KBr, cmꢁ1) Vmax