5
7.28 (d, J = 8.0 Hz, 2H), 4.34(s, 2H), 2.43(s, 3H); 13C NMR
6.0 Hz, 3H ); 13C NMR (100MHz, CDCl ) δ 202.31, 39.87, 34.42,
31.90, 29.34, 29.04, 29.26, 29.24 28.96, 23.86, 22.70, 14.15.
ACCEPTED MANUSCRIPT
3
(100Mz, CDCl3) δ 190.50, 142.85, 128.94, 127.56, 127.18, 19.80.
1-(4-bromophenyl)-2-iodoethanone 2ad3p: Colorless solid (74.8
6-(benzyloxy)-1-bromohexan-2-one 2s5 : Colorless oil (57.9 mg,
68% yield); H NMR (400 MHz, CDCl3) δ 7.37-7.25 (m, 5H),
4.48 (s, 2H), 3.85 (s, 2H), 3.46 (t, J = 6.0 Hz, 2H), 2.67 (t, J = 8.0
Hz, 2H), 1.77-1.68 (m, 2H), 1.67-1.58 (m, 2H); 13C NMR
(100Mz, CDCl3) δ 200.94, 137.40, 127.36, 126.65, 126.57, 71.92,
68.81, 38.43, 33.29, 27.91, 19.71.
1
1
mg, 77% yield); H NMR (400 MHz, CDCl3) δ 7.82 (d, J = 8.0
Hz, 2H), 7.60 (d, J = 8.0 Hz, 2H), 4.30(s, 2H); 13C NMR (100Mz,
CDCl3) δ 190.57, 130.90, 130.88, 129.23, 127.82.
Acknowledgments
6-bromo-5-oxohexyl acetate 2t5: Colorless oil (46.0 mg, 65%
yield); H NMR (400 MHz, CDCl3) δ 4.07 (t, J = 6.0 Hz, 2H),
3.90 (s, 2H), 2.71 (t, J = 6.0, 2H), 2.05 (s, 3H), 1.74-1.63 (m, 4H);
13C NMR (100MHz, CDCl3) δ 200.68, 170.14, 62.88, 38.10,
33.18, 26.80, 19.96, 19.19.
This research was financially supported by Chinese National
Natural Science Foundation (No. 81302456), China Postdoctoral
Science Special Foundation (No. 2014T70792), China
Postdoctoral Science Foundation (No. 2013M542144),
Specialized Research Fund for the Doctoral Program of Higher
Education (No. 20130162120076) and Research Foundation of
Education Bureau of Hunan Province, China (No. 15B095).
1
1-bromo-6-chlorohexan-2-one 2u5 : Colorless oil (47.7 mg,
75% yield); 1H NMR (400 MHz, CDCl3) δ 3.86 (s, 2H), 3.51 (t, J
= 6.0 Hz, 2H), 2.68 (t, J = 8.0 Hz, 2H),1.79-1.72 (m,4H); 13
C
Supplementary data
NMR (100Mz, CDCl3) δ 200.55, 43.51, 37.77, 33.14, 30.60,
20.04.
Supplementary data associated with this article can be found
in the online version, at
1,6-dibromohexan-2-one 2v5 : Colorless oil (56.5 mg, 73%
yield); 1H NMR (400 MHz, CDCl3) δ 3.88 (s, 2H), 3.40 (t, J = 6.0
Hz, 2H), 2.70 (t, J = 8.0 Hz, 2H),1.90-1.82 ( m, 2H), 1.81-1.73
(m, 2H); 13C NMR (100Mz, CDCl3) δ 201.67, 38.69, 34.19,
33.19, 31.75, 22.28.
References and notes
(1) (a) Erian, A.; Sherif, S.; Gaber, H. Molecules 2003, 8, 793; (b)
Moiseev, I. K.; Makarova, N. V.; Zemtsova, M. N. Russ. J. Org.
Chem. 2003, 39, 1685-1701; (c) Krauze, A.; Vilums, M.; Sile, L.;
Duburs, G. Heterocycl. Commun. 2009, 15, 239-244.
2-bromo-1-(cyclohex-1-en-1-yl)ethanone 2w5 : Colorless oil
(52.1 mg, 86% yield); 1H NMR (400 MHz, CDCl3) δ 6.97 (t, J =
4.0 Hz, 1H), 4.15 (s, 2H), 2.30-2.22 (m, 4H), 1.66-1.58 (m, 4H);
13C NMR (100MHz, CDCl3) δ 191.21, 141.88, 135.84, 29.06,
25.25, 22.25, 20.71, 20.28.
(2) (a) Xiao, F.; Chen, D.; Luo, L.; Zhong, X.; Xie, Y.; Zou, L.;
Zeng, M.; Guan, L.; Zhong, C. Molecular medicine reports 2013, 8,
53-60; (b) Montgomery, J. A.; Thomas, H. J.; Brockman, R. W.;
Elliott, R. D. J. Med. Chem. 1984, 27, 680-684; (c) Whitten, J. P.;
Cube, R. V.; Baron, B. M.; McDonald, I. A. Bioorg. Med. Chem.
Lett. 1993, 3, 19-22; (d) Liu, P.; Liu, A.; Yan, F.; Wolfe, M. D.;
Lipscomb, J. D.; Liu, H.-w. Biochemistry 2003, 42, 11577-11586; (e)
Li, X.; Bhandari, A.; Holmes, C. P.; Szardenings, A. K. Bioorg. Med.
Chem. Lett. 2004, 14, 4301-4306; (f) Somu, R. V.; Boshoff, H.; Qiao,
C.; Bennett, E. M.; Barry, C. E.; Aldrich, C. C. J. Med. Chem. 2005,
49, 31-34; (g) Bernier, S.; Akochy, P.-M.; Lapointe, J.; Chênevert, R.
Biorg. Med. Chem. 2005, 13, 69-75; (h) Balg, C.; Blais, S. P.;
Bernier, S.; Huot, J. L.; Couture, M.; Lapointe, J.; Chênevert, R.
Biorg. Med. Chem. 2007, 15, 295-304; (i) Paterson, I.; Gardner, N.
M.; Poullennec, K. G.; Wright, A. E. Bioorg. Med. Chem. Lett. 2007,
17, 2443-2447; (j) Perumal, S. K.; Adediran, S. A.; Pratt, R. F. Biorg.
Med. Chem. 2008, 16, 6987-6994; (k) Zubarev, A. A.; Larionova, N.
A.; Rodinovskaya, L. A.; Mortikov, V. Y.; Shestopalov, A. M. Acs
Combinatorial Science 2013, 15, 546-550; (l) Xiao, F.; Li, Y.; Luo,
L.; Xie, Y.; Zeng, M.; Wang, A.; Chen, H.; Zhong, C. Cell. Physiol.
Biochem. 2014, 33, 1013-1025.
(3) (a) Cardillo, G.; Shimizu, M. J. Org. Chem. 1977, 42, 4268-
4270; (b) Calò, V.; Lopez, L.; Valentino, D. S. Synthesis 1978, 139-
140; (c) Hoffmann, H. M. R.; Haase, K. Synthesis 1981, 715-719; (d)
Olah, G. A.; Ohannesian, L.; Arvanaghi, M.; Prakash, G. K. S. J. Org.
Chem. 1984, 49, 2032-2034; (e) Morton, H. E.; Leanna, M. R.
Tetrahedron Lett. 1993, 34, 4481-4484; (f) VanBrunt, M. P.;
Ambenge, R. O.; Weinreb, S. M. J. Org. Chem. 2003, 68, 3323-3326;
(g) Xu, Z.; Zhang, D.; Zou, X. Synth. Commun. 2006, 37, 255-258;
(h) Arbuj, S. S.; Waghmode, S. B.; Ramaswamy, A. V. Tetrahedron
Lett. 2007, 48, 1411-1415; (i) Yin, G.; Gao, M.; She, N.; Hu, S.; Wu,
A.; Pan, Y. Synthesis 2007, 3113-3116; (j) Adimurthy, S.; Ghosh, S.;
Patoliya, P. U.; Ramachandraiah, G.; Agrawal, M.; Gandhi, M. R.;
2-bromo-1-cyclohexylethanone 2x5 : Colorless oil (51.4 mg,
1
84% yield); H NMR (400 MHz, CDCl3) δ 3.95 (s, 2H), 2.71-
2.64 (m, 1H), 1.87-1.73 (m, 4H), 1.68-1.64(m, 1H), 1.41-1.17(m,
5H); 13C NMR (100MHz, CDCl3) δ 204.68, 48.03, 33.53, 28.70,
25.63., 25.48.
2-chloro-1-phenylethanone 2y5: Colorless solid (41.6 mg, 90%
1
yield); H NMR (400 MHz, CDCl3) δ 7.94 (d, J = 8.0 Hz, 2H),
7.61 (t, J = 8.0 Hz, 1H), 7.49(t, J = 8.0 Hz, 2H), 4.71(s, 2H); 13
C
NMR (100MHz, CDCl3) δ 191.13, 134.24, 134.04, 128.93,
128.53, 46.08.
2-chloro-1-(p-tolyl)ethanone 2z6: Colorless solid (45.4 mg, 90%
1
yield); H NMR (400 MHz, CDCl3) δ 7.85 (d, J = 8.0, 2H), 7.28
(d, J = 8.0, 2H), 4.67(s, 2H), 2.42(s, 3H); 13C NMR (100MHz,
CDCl3) δ 190.73,149.22, 145.06, 129.59, 128.66, 45.92, 21.75.
1-(4-bromophenyl)-2-chloroethanone 2aa3l: Colorless solid
1
(55.0 mg, 79% yield) H NMR (400 MHz, CDCl3) δ 7.81 (d, J =
8.0 Hz, 2H), 7.63 (d, J = 8.0 Hz, 2H), 4.64(s, 2H); 13C NMR
(100Mz, CDCl3) δ 190.27, 132.91, 132.28, 130.05, 129.37, 45.58.
2-iodo-1-phenylethanone 2ab3p: Colorless solid (62.7 mg, 85%
1
yield); H NMR (400 MHz, CDCl3) δ 7.99 (d, J = 4.0 Hz, 2H),
7.59 (t, J = 8.0 Hz, 1H), 7.48 (t, J = 8.0 Hz, 2H), 4.36 (s, 2H); 13
C
NMR (100Mz, CDCl3) δ 191.16, 132.16, 131.78, 127.37, 127.17.
2-iodo-1-(p-tolyl)ethanone 2ac3p: Colorless solid (68.6 mg, 88%
1
yield); H NMR (400 MHz, CDCl3) δ 7.89 (d, J = 8.0 Hz, 2H),