Page 5 of 8
New Journal of Chemistry
Please do not adjust margins
Journal Name
ARTICLE
1
2
3
4
5
6
7
8
9
2-bromo-4-fluorobenzamide (3b): The crude product was (petroleum ether/ethyl acetate = 5:1) to give 3i as white solid
DOI: 10.1039/C8NJ06023A
1
purified by column chromatography on silica gel (petroleum (93.34mg, 75%). H NMR (500 MHz, Chloroform-d) δ 8.20 (dd, J
ether/ethyl acetate = 5:1) to give 3b as white solid (85.72mg, = 7.8, 1.8 Hz, 1H), 7.79 (dd, J = 7.9, 1.3 Hz, 1H), 7.60 – 7.29 (m,
1
79%). H NMR (500 MHz, Chloroform-d) δ 7.71 (dd, J = 8.7, 6.0 3H), 2.66 (s, 3H). 13C NMR (126 MHz, Chloroform-d) δ 136.6,
Hz, 1H), 7.37 (dd, J = 8.2, 2.5 Hz, 1H), 7.14 – 7.08 (m, 1H), 6.16 134.1, 132.8, 131.1, 126.9, 118.6, 28.3. GC-MS (EI) m/z: 249.
(s, 1H), 6.03 (s, 1H).1H NMR (500 MHz, Chloroform-d) δ 7.71 (dd,
2-bromo-N,4-dimethylbenzenesulfonamide (3j): The crude
J = 8.7, 6.0 Hz, 1H), 7.37 (dd, J = 8.2, 2.5 Hz, 1H), 7.14 – 7.08 (m, product was purified by column chromatography on silica gel
1H), 6.14 (s, 1H), 6.04 (s, 1H). 13C NMR (126 MHz, Chloroform-d) (petroleum ether/ethyl acetate = 5:1) to give 3j as white solid
δ 167.1, 163.2, 131.7, 130.9, 120.1, 119.9, 114.1, 114.0. GC-MS (93.37mg, 71%). 1H NMR (500 MHz, Chloroform-d) δ 8.01 (d, J =
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
(EI) m/z: 217.
8.1 Hz, 1H), 7.56 (dd, J = 1.7, 0.8 Hz, 1H), 7.28 – 7.26 (m, 1H),
2-bromo-4-chlorobenzamide (3c): The crude product was 2.60 (d, J = 5.4 Hz, 3H), 2.41 (s, 3H). 13C NMR (126 MHz,
purified by column chromatography on silica gel (petroleum Chloroform-d) δ 144.1, 134.5, 133.6, 131.1, 127.5, 118.4, 28.3,
ether/ethyl acetate = 5:1) to give 3c as white solid (89.71mg, 20.1. GC-MS (EI) m/z: 263.
77%). 1H NMR (500 MHz, Chloroform-d) δ 7.68 – 7.58 (m, 2H),
7.38 (dd, J = 8.3, 2.0 Hz, 1H), 6.15 (s, 1H), 6.00 (s, 1H). 13C NMR purified by column chromatography on silica gel (petroleum
(126 MHz, Chloroform-d) δ 167.2, 136.2, 133.9, 132.3, 130.1, ether/ethyl acetate = 5:1) to give 3k as white solid (81.32mg,
methyl 2-bromobenzoate (3k): The crude product was
127.0, 118.8. GC-MS (EI) m/z: 233.
76%). 1H NMR (500 MHz, Chloroform-d) δ 7.77 (dd, J = 7.5, 2.0
2-bromo-4-methylbenzamide (3d): The crude product was Hz, 1H), 7.64 (dd, J = 7.8, 1.5 Hz, 1H), 7.38 – 7.27 (m, 2H), 3.92
purified by column chromatography on silica gel (petroleum (s, 3H). 13C NMR (126 MHz, Chloroform-d) δ 165.6, 133.3, 131.6,
ether/ethyl acetate = 5:1) to give 3d as white solid (72.42mg, 131.2, 130.3, 126.2, 120.6, 51.5. GC-MS (EI) m/z: 214.
68%). 1H NMR (500 MHz, DMSO-d6) δ 7.72 (s, 1H), 7.43 (s, 2H),
7.25 (d, J = 7.7 Hz, 1H), 7.19 – 7.14 (m, 1H), 2.27 (s, 3H). 13C NMR by column chromatography on silica gel (petroleum ether/ethyl
(126 MHz, DMSO-d6) δ 168.5, 140.2, 135.8, 132.4, 127.9, 127.5, acetate = 5:1) to give 3l as white solid (74.90mg, 70%). 1H NMR
ethyl 2-bromobenzoate (3l): The crude product was purified
118.0, 19.8. GC-MS (EI) m/z: 213.
(500 MHz, Chloroform-d) δ 7.78 (dd, J = 7.6, 1.9 Hz, 1H), 7.65
2-bromo-N-methylbenzamide (3e): The crude product was (dd, J = 7.8, 1.4 Hz, 1H), 7.40 – 7.28 (m, 2H), 4.41 (q, J = 7.1 Hz,
purified by column chromatography on silica gel (petroleum 2H), 1.41 (t, J = 7.2 Hz, 3H). 13C NMR (126 MHz, Chloroform-d) δ
ether/ethyl acetate = 5:1) to give 3e as white solid (77.75mg, 165.3, 133.3, 131.6, 131.4, 130.2, 126.2, 120.5, 60.6, 13.2. GC-
73%). 1H NMR (500 MHz, Chloroform-d) δ 7.63 (dd, J = 8.0, 1.2 MS (EI) m/z: 228.
Hz, 1H), 7.57 (dd, J = 7.6, 1.8 Hz, 1H), 7.42 – 7.37 (m, 1H), 7.33 –
7.29 (m, 1H), 6.07 (s, 1H), 3.07 (d, J = 4.9 Hz, 3H). 13C NMR (126 column chromatography on silica gel (petroleum ether/ethyl
MHz, Chloroform-d) δ 167.3, 136.9, 132.4, 130.2, 128.6, 126.6, acetate = 5:1) to give 4a as white solid (100.04mg, 81%). 1H NMR
2-iodobenzamide (4a): The crude product was purified by
118.3, 25.8. GC-MS (EI) m/z: 213.
(500 MHz, DMSO-d6) δ 7.85 (d, J = 7.9 Hz, 1H), 7.80 (s, 1H), 7.49
2-bromo-N-(tert-butyl)benzamide (3f): The crude product (s, 1H), 7.41 (t, J = 7.4 Hz, 1H), 7.33 (dd, J = 7.5, 1.7 Hz, 1H), 7.13
was purified by column chromatography on silica gel (td, J = 7.6, 1.8 Hz, 1H). 13C NMR (126 MHz, DMSO-d6) δ 170.1,
(petroleum ether/ethyl acetate = 5:1) to give 3f as white solid 142.6, 138.6, 130.0, 127.4, 127.2, 92.6. GC-MS (EI) m/z: 247.
(89.25mg, 70%). 1H NMR (500 MHz, Chloroform-d) δ 7.56 (dd, J
= 8.0, 1.2 Hz, 1H), 7.50 – 7.48 (m, 1H), 7.35 – 7.31 (m, 1H), 7.26 purified by column chromatography on silica gel (petroleum
– 7.21 (m, 1H), 5.73 (s, 1H), 1.48 (s, 9H). 13C NMR (126 MHz, ether/ethyl acetate = 5:1) to give 4b as white solid (99.18mg,
2-iodo-N-methylbenzamide (4b): The crude product was
1
Chloroform-d) δ 166.0, 138.1, 132.2, 130.8, 129.9, 128.3, 126.5, 76%). H NMR (500 MHz, Chloroform-d) δ 7.92 – 7.77 (m, 1H),
51.3, 27.8. GC-MS (EI) m/z: 255.
7.48 – 7.32 (m, 2H), 7.10 (m, 1H), 5.77 (s, 1H), 3.03 (d, J = 4.9 Hz,
2,4-dibromo-N-methylbenzamide (3g): The crude product 3H). 13C NMR (126 MHz, Chloroform-d) δ 169.1, 141.4, 138.9,
was purified by column chromatography on silica gel 130.1, 127.2, 126.8, 91.5, 25.8. GC-MS (EI) m/z: 261.
(petroleum ether/ethyl acetate = 5:1) to give 3g as white solid
methyl 2-iodobenzoate (4c): The crude product was purified
(92.30mg, 63%). 1H NMR (500 MHz, Chloroform-d) δ 7.80 (d, J = by column chromatography on silica gel (petroleum ether/ethyl
1.8 Hz, 1H), 7.53 (dd, J = 8.2, 1.8 Hz, 1H), 7.44 (d, J = 8.2 Hz, 1H), acetate = 5:1) to give 4c as white solid (100.87mg, 77%). 1H NMR
6.13 (s, 1H), 3.05 (d, J = 4.9 Hz, 3H). 13C NMR (126 MHz, (500 MHz, Chloroform-d) δ 7.97 (dd, J = 8.0, 1.1 Hz, 1H), 7.78
Chloroform-d) δ 166.3, 135.7, 134.8, 133.0, 129.8, 123.5, 119.0, (dd, J = 7.8, 1.7 Hz, 1H), 7.38 (td, J = 7.6, 1.1 Hz, 1H), 7.13 (td, J
25.8. GC-MS (EI) m/z: 293.
= 7.6, 1.8 Hz, 1H), 3.92 (s, 3H).13C NMR (126 MHz, Chloroform-
2-bromo-4-methoxybenzenesulfonamide (3h): The crude d) δ 165.9, 140.3, 134.1, 131.7, 130.0, 126.9, 93.1, 51.5. GC-MS
product was purified by column chromatography on silica gel (EI) m/z: 262.
(petroleum ether/ethyl acetate = 5:1) to give 3h as white solid
(91.43mg, 69%). 1H NMR (500 MHz, Chloroform-d) δ 8.11 (d, J = column chromatography on silica gel (petroleum ether/ethyl
2.3 Hz, 1H), 7.87 (dd, J = 8.6, 2.3 Hz, 1H), 6.97 (d, J = 8.7 Hz, 1H), acetate = 5:1) to give 4d as white solid (54.25mg, 70%). 1H NMR
3.98 (s, 3H). 13C NMR (126 MHz, Chloroform-d) δ 158.8, 133.8, (500 MHz, Chloroform-d) δ 7.85 – 7.74 (m, 1H), 7.57 – 7.32 (m,
130.9, 126.6, 111.4, 110.4, 55.7. GC-MS (EI) m/z: 265.
2-bromo-N-methylbenzenesulfonamide (3i): The crude δ 167.5, 132.9, 130.8, 129.9, 129.6, 129.4, 126.2. GC-MS (EI) m/z:
product was purified by column chromatography on silica gel 155.
2-chlorobenzamide (4d): The crude product was purified by
3H), 6.69 (s, 1H), 6.46 (s, 1H). 13C NMR (126 MHz, Chloroform-d)
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 5
Please do not adjust margins