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PAPER
5 equiv) under ice-cooling. After stirring overnight at r.t., the mix-
ture was poured into ice water (100 mL). The precipitated yellow
solid was dissolved in EtOAc (50 mL), the aqueous phase was ex-
tracted with EtOAc (50 mL) and the organic phase was washed with
sat. aq NaHCO3 (50 mL), brine (50 mL) and dried over MgSO4. Af-
ter removing the solvent under vacuum, 9 was obtained as a yellow
solid.
(5) Schäfer, C.; Herrmann, F.; Mattay, J. Beilstein J. Org. Chem.
2008, 4, 41; doi: 10.3762/bjoc.4.41.
(6) Fages, F.; Desvergne, J.-P.; Frisch, I.; Bouas-Laurent, H.
J. Chem. Soc., Chem. Commun. 1988, 1414.
(7) (a) Toyota, S.; Goichi, M.; Kotani, M. Angew. Chem. Int. Ed.
2004, 43, 2248; Angew. Chem. 2004, 116, 2298. (b)Vögtle,
F.; Koch, H.; Rissanen, K. Chem. Ber. 1992, 125, 2129.
(c) Brettar, J.; Gisselbrecht, J.-P.; Gross, M.; Solladié, N.
Chem. Commun. 2001, 733. (d) Bar, A. K.; Gole, B.; Ghosh,
S.; Mukherjee, P. S. Dalton Trans. 2009, 6701. (e) Ghosh,
S.; Chakrabarty, R.; Mukherjee, P. S. Inorg. Chem. 2009, 48,
549. (f) Katz, H. E. J. Org. Chem. 1989, 54, 2179.
(g) Kauffman, J. M. Synthesis 2001, 197. (h) Effenberger,
F.; Heid, S.; Merkle, R.; Zimmermann, P. Synthesis 1995,
1115. (i) Yagodkin, E.; Douglas, C. J. Tetrahedron Lett.
2010, 51, 3037. (j) Rein, R.; Gross, M.; Solladié, N. Chem.
Commun. 2004, 1992. (k) Flamingni, L.; Talarico, A. M.;
Ventura, B.; Rein, R.; Solladié, N. Chem. Eur. J. 2006, 12,
701. (l) House, H. O.; Hrabie, J. A.; VanDerveer, D. J. Org.
Chem. 1986, 51, 921. (m) Synthesis of 1,5-dichloroanthra-
cene (1) is analogous to the described synthesis7l of 1,8-
dichloroanthracene.
Yield: 40 mg (0.10 mmol, 91%, corrected yield because EtOAc
could not be removed completely under vacuum).
1H NMR (DMSO-d6): d = 6.81–6.85 (m, 2 H, ArH), 6.91–6.97 (m,
3
4 H, ArH), 7.33 (d, J = 6.6 Hz, 2 H, ArH), 7.44–7.49 (m, 2 H,
ArH), 7.96 (d, 3J = 8.6 Hz, 2 H, ArH), 8.55 (s, 2 H, ArH), 9.11 (s,
2 H, OH), 9.14 (s, 2 H, OH).
13C NMR (DMSO-d6): d = 115.8, 117.2, 120.8, 124.9, 125.2, 126.0,
127.6, 129.6, 131.2, 131.7, 139.6, 145.1, 145.2.
HRMS (EI): m/z calcd for C26H18O4: 394.12051; found: 394.12030.
Acknowledgment
Support by the Deutsche Forschungsgemeinschaft (SFB 613) is
gratefully acknowledged.
(8) (a) Rosen, B. M.; Quasdorf, K. W.; Wilson, D. A.; Zhang,
N.; Resmerita, A.-M.; Garg, N. K.; Percec, V. Chem. Rev.
2011, 111, 1346. (b) Jana, R.; Pathak, T. P.; Sigman, M. S.
Chem. Rev. 2011, 111, 1417.
References
(9) (a) Clar, E.; Mackay, C. C. Tetrahedron 1972, 28, 5049.
(b) Cristol, S. J.; Caspar, M. L. J. Org. Chem. 1967, 33,
2020.
(1) Fritzsche, J. C. R. Hebd. Seances Acad. Sci. 1867, 69, 1035.
(2) (a) Becker, H. D. Chem. Rev. 1993, 93, 145. (b) Bouas-
Laurent, H.; Castellan, A.; Desvergne, J.-P.; Lapouyade, R.
Chem. Soc. Rev. 2000, 29, 43. (c) Bouas-Laurent, H.;
Castellan, A.; Desvergne, J.-P.; Lapouyade, R. Chem. Soc.
Rev. 2001, 30, 248.
(3) (a) Zhang, G.; Zhang, D.; Ziao, X.; Ai, X.; Zhang, J.; Zhu,
D. Chem. Eur. J. 2006, 12, 1067. (b) Kim, S. K.; Singh, N.
J.; Kim, S. J.; Kim, H. G.; Kim, J. K.; Lee, J. W.; Kim, K. S.;
Yoon, J. Org. Lett. 2003, 5, 2083. (c) Kim, Y. K.; Lee, H.
N.; Singh, N. J.; Choi, H. J.; Xue, J. Y.; Kim, K. S.; Yoon,
J.; Hyun, M. H. J. Org. Chem. 2008, 73, 301.
(10) For examples from numerous reports in the literature, see:
(a) Martinez, G. R.; Garcia, F.; Catalani, L. H.; Cadet, J.;
Oliveira, M. C. B.; Ronsein, G. E.; Miyamoto, S.; Medeiros,
M. H. G.; Di Mascio, P. Tetrahedron 2006, 62, 10762.
(b) Barton, D. H. R.; Hui, R. A. H. F.; Lester, D. J.; Ley, S.
V. Tetrahedron Lett. 1979, 3331. (c) Koeberg-Telder, A.;
Cerfontain, H. Tetrahedron Lett. 1974, 3535. (d) Tanko, J.
M.; Wang, Y. Chem. Commun. 1997, 2387.
(11) (a) Kitagawa, K.; Inoue, A.; Shinokubo, H.; Oshima, K.
Angew. Chem. Int. Ed. 2000, 39, 2481; Angew. Chem. 2000,
112, 2594. (b) Inoue, A.; Kitagawa, K.; Shinikubo, H.;
Oshima, K. J. Org. Chem. 2001, 66, 4333.
(d) Nishimura, G.; Maehara, H.; Shiraishi, Y.; Hirai, T.
Chem. Eur. J. 2008, 14, 259. (e) Shirtcliff, L. D.; Xu, H.;
Diederich, F. Eur. J. Org. Chem. 2010, 846.
(12) Lau, S. Y. W.; Hughes, G.; O’Shea, P. D.; Davies, I. W. Org.
(f) Kaanumalle, L. S.; Gibb, C. L. D.; Gibb, B. C.;
Ramamurthy, V. J. Am. Chem. Soc. 2005, 127, 3674.
(g) Jayaraj, N.; Zhao, Y.; Parthasarathy, A.; Porel, M.; Liu,
R. S. H.; Ramamurthy, V. Langmuir 2009, 25, 10575.
(h) Tosic, O.; Mattay, J. Eur. J. Org. Chem. 2011, 371.
(4) (a) Schäfer, C.; Eckel, R.; Ros, R.; Mattay, J.; Anselmetti, D.
J. Am. Chem. Soc. 2007, 129, 1488. (b) Schäfer, C.; Strübe,
F.; Bringmann, S.; Mattay, J. Photochem. Photobiol. Sci.
2008, 7, 1457. (c) Molard, Y.; Bassani, D. M.; Desvergne,
J.-P.; Moran, N.; Tucker, J. H. R. J. Org. Chem. 2006, 71,
8523. (d) Okada, M.; Harada, A. Macromolecules 2003, 36,
9701. (e) Toyota, S.; Kuga, M.; Takatsu, A.; Goichi, M.;
Iwanaga, T. Chem. Commun. 2008, 1323. (f) Cao, D.;
Meier, H. Angew. Chem. Int. Ed. 2001, 40, 186; Angew.
Chem. 2001, 113, 193. (g) Gassensmith, J. J.; Baumes, J.
M.; Eberhard, J.; Smith, B. D. Chem. Commun. 2009, 2517.
(h) Gassensmith, J. J.; Arunkumar, E.; Barr, L.; Baumes, J.
M.; DiVittorio, K. M.; Johnson, J. R.; Noll, B. C.; Smith, B.
D. J. Am. Chem. Soc. 2007, 129, 15054.
Lett. 2007, 9, 2239.
(13) Cashman, J. R.; Voelker, T.; Zhang, H.-T.; O’Donnell, J. M.
J. Med. Chem. 2009, 52, 1530.
(14) Sakata, Y.; Toyoda, T.; Misumi, S. Tetrahedron Lett. 1992,
33, 5077.
(15) Bringmann S., Brodbeck R., Hartmann R., Schäfer C.,
Mattay J. to be published
(16) Palazzott, M. C.; Rakow, N. A.; Wendland, M. S.
Fluorescent chemical sensor, U.S. Pat. Appl. Publ. G01N 33/
50 20060101 G01N033/50, 2008.
(17) Osuka, A.; Fujikane, D.; Shinmori, H.; Kobatake, S.; Irie, M.
J. Org. Chem. 2001, 66, 3913.
Synthesis 2011, No. 14, 2291–2296 © Thieme Stuttgart · New York