The Journal of Organic Chemistry
Page 10 of 14
1
2
3
4
5
HRMS (DART Positive) calcd for: C15H10O2F [MꢀH]ꢀ 241.0659; found: 241.0658.
Benzofuranꢀ2ꢀyl(4ꢀbromophenyl)methanol (2g). Product was isolated via column
1
chromatography (PE/EA 4:1) as yellow oil (60.6 mg, 80%). H NMR (500 MHz, CDCl3) δ
6
7.52 (ddd, J = 8.4, 3.8, 2.8 Hz, 3H), 7.44 (dd, J = 8.2, 0.7 Hz, 1H), 7.37 – 7.33 (m, 2H), 7.30
– 7.25 (m, 1H), 7.24 – 7.20 (m, 1H), 6.51 (d, J = 4.7 Hz, 1H), 5.95 – 5.81 (m, 1H), 2.95 –
2.63 (m, 1H); 13C NMR (126 MHz, CDCl3) δ 157.9, 155.1, 139.2, 131.7, 128.5, 127.9, 124.6,
123.0, 122.3, 121.2, 111.4, 104.3, 69.9; HRMS (DART Positive) calcd for: C15H10O2Br
[MꢀH]ꢀ 300.9859; found: 300.9858.
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Benzofuranꢀ2ꢀyl(2ꢀchlorophenyl)methanol (2h). Product was isolated via column
1
chromatography (PE/EA 4:1) as yellow oil (58.9 mg, 91%). H NMR (500 MHz, CDCl3) δ
7.72 (dd, J = 7.6, 1.8 Hz, 1H), 7.56 – 7.52 (m, 1H), 7.51 – 7.47 (m, 1H), 7.44 – 7.40 (m, 1H),
7.37 (ddd, J = 9.0, 5.5, 1.4 Hz, 1H), 7.34 – 7.28 (m, 2H), 7.24 (ddd, J = 10.9, 4.4, 2.2 Hz, 1H),
6.50 (t, J = 0.8 Hz, 1H), 6.36 (t, J = 17.8 Hz, 1H), 3.03 (t, J = 7.2 Hz, 1H); 13C NMR (126
MHz, CDCl3) δ 157.0, 155.1, 137.7, 132.7, 129.6, 129.5, 128.4, 127.9, 127.2, 124.5, 122.9,
121.3, 111.4, 104.7, 67.3; HRMS (DART Positive) calcd for: C15H10O2Cl [MꢀH]ꢀ 257.0364;
found: 257.0362.
Benzofuranꢀ2ꢀyl(2ꢀmethoxyphenyl)methanol (2i). Product was isolated via column
1
chromatography (PE/EA 4:1) as yellow oil (53.3 mg, 84%). H NMR (500 MHz, CDCl3) δ
7.55 – 7.52 (m, 1H), 7.50 – 7.47 (m, 1H), 7.42 (dd, J = 7.5, 1.6 Hz, 1H), 7.39 – 7.34 (m, 1H),
7.30 – 7.26 (m, 1H), 7.23 (td, J = 7.5, 1.0 Hz, 1H), 7.03 (td, J = 7.5, 0.9 Hz, 1H), 6.97 (d, J =
8.2 Hz, 1H), 6.52 (s, 1H), 6.21 (d, J = 6.1 Hz, 1H), 3.87 (s, 3H), 3.39 (t, J = 13.4 Hz, 1H); 13C
NMR (126 MHz, CDCl3) δ 158.5, 156.9, 155.0, 129.5, 128.5, 128.3, 128.2, 124.0, 122.7,
121.0, 120.9, 111.4, 110.9, 103.6, 67.2, 55.6; HRMS (DART Positive) calcd for: C16H13O3
[MꢀH]ꢀ 253.0859; found: 253.0858.
Benzofuranꢀ2ꢀyl(naphthalenꢀ1ꢀyl)methanol (2j). Product was isolated via column
chromatography (PE/EA 4:1) as white solid (51.4 mg, 75%), mp 82.4ꢀ85.7oC. 1H NMR (500
MHz, CDCl3) δ 8.30 (s, 1H), 8.24 – 8.17 (m, 3H), 7.91 (dd, J = 8.6, 1.7 Hz, 1H), 7.89 – 7.83
(m, 3H), 7.80 (dd, J = 8.2, 0.7 Hz, 1H), 7.65 – 7.59 (m, 1H), 7.59 – 7.54 (m, 1H), 6.89 (t, J =
0.8 Hz, 1H), 6.44 (d, J = 3.6 Hz, 1H), 3.28 (d, J = 4.1 Hz, 1H); 13C NMR (126 MHz, CDCl3)
δ 158.5, 155.1, 137.6, 133.3, 133.2, 128.5, 128.2, 128.1, 127.8, 126.4, 126.4, 125.8, 124.6,
124.4, 122.9, 121.2, 111.4, 104.3, 70.8; HRMS (DART Positive) calcd for: C19H13O2 [MꢀH]ꢀ
273.0910; found: 273.0909.
Benzofuranꢀ2ꢀyl(3ꢀchlorophenyl)methanol (2k). Product was isolated via column
1
chromatography (PE/EA 4:1) as yellow oil (51.7 mg, 80%). H NMR (500 MHz, CDCl3) δ
7.56 – 7.50 (m, 2H), 7.45 (dd, J = 8.2, 0.6 Hz, 1H), 7.38 – 7.34 (m, 1H), 7.34 – 7.30 (m, 2H),
7.28 (dt, J = 7.4, 1.7 Hz, 1H), 7.23 (ddd, J = 10.7, 4.3, 2.2 Hz, 1H), 6.54 (d, J = 0.5 Hz, 1H),
5.90 (s, 1H), 3.00 – 2.67 (m, 1H); 13C NMR (126 MHz, CDCl3) δ 157.7, 155.1, 142.2, 134.53,
129.9, 128.5, 127.9, 126.9, 124.9, 124.6, 123.0, 121.3, 111.4, 104.3, 69.9; HRMS (DART
Positive) calcd for: C15H10O2Cl [MꢀH]ꢀ 257.0364; found: 257.0363.
Benzofuranꢀ2ꢀyl(3ꢀmethoxyphenyl)methanol (2l). Product was isolated via column
1
chromatography (PE/EA 4:1) as yellow oil (54.6 mg, 86%). H NMR (500 MHz, CDCl3) δ
7.57 – 7.52 (m, 1H), 7.46 (dt, J = 15.4, 7.6 Hz, 1H), 7.33 (t, J = 7.8 Hz, 1H), 7.29 (ddd, J =
8.2, 6.6, 1.4 Hz, 1H), 7.24 (td, J = 7.6, 1.0 Hz, 1H), 7.09 (dd, J = 9.4, 1.5 Hz, 2H), 7.00 – 6.85
(m, 1H), 6.56 (s, 1H), 5.93 (d, J = 3.7 Hz, 1H), 3.83 (s, 3H), 2.96 (dd, J = 78.4, 5.1 Hz, 1H);
ACS Paragon Plus Environment