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    188宝金博页面版: A new synthetic approach towards 7-substituted 2-alkyl-2,3,4,9-tetrahydro-1

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    内容提示： Russian Chemical Bulletin, International Edition, Vol. 60, No. 10, pp. 2114—2116, October, 2011 2114Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2077—2079, October, 2011.1066?5285/11/6010?2114 ? 2011 Springer Science+Business Media, Inc.A new synthetic approach towards 7?substituted2?alkyl?2,3,4,9?tetrahydro?1H?fluorenesV. V. Mezhnev and R. Ch. GeivandovFine Organic Synthesis and Organic Functional materials, INCORFIN, Ltd,27 ul. Burakova, 105118 Moscow, Russian Fed...

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    Russian Chemical Bulletin, International Edition, Vol. 60, No. 10, pp. 2114—2116, October, 2011 2114Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2077—2079, October, 2011.1066?5285/11/6010?2114 © 2011 Springer Science+Business Media, Inc.A new synthetic approach towards 7?substituted2?alkyl?2,3,4,9?tetrahydro?1H?fluorenesV. V. Mezhnev and R. Ch. GeivandovFine Organic Synthesis and Organic Functional materials, INCORFIN, Ltd,27 ul. Burakova, 105118 Moscow, Russian Federation.E?mail: r.ch.geivandov@gmail.comCyclization of 2?(4?bromophenyl)?5?pentylcyclohex?1?ene?1?carboxylic acid followed byreduction of the carbonyl group resulted in the corresponding 7?substituted derivative of 2?alkyl?2,3,4,9?tetrahydro?1H?fluorene.Key words: β ?chloroenal, fluorenes, cross?couplingIn continuation of our study 1—3 in the field of liquidcrystal structures bearing mono?, bi?, and tricyclic frag?ments, we developed a synthetic route towards key inter?mediates for preparing the novel class of liquid crystals,7?substituted derivatives of 2?alkyl?2,3,4,9?tetrahydro?1H?fluorene. 4In the present work, we report synthetic approach to?wards hitherto unknown 7?bromo?2?pentyl?2,3,4,9?tetra?hydro?1H?fluorene (1) (Scheme 1).Formylation of 4?pentylcyclohexanone (2) with a mix?ture of phosphorus oxychloride and DMF in chloroformaccording to the Vilsmeier—Haack—Arnold procedure 5Scheme 1i. 1) POCl 3 , HC(O)NMe 2 , CHCl 3 , 5–10 ° C, 10 min, 2) 1, 50—60 ° C, 3 h; ii. 4?BrC 6 H 4 B(OH) 2 , BuNBr, 10% Pd/C, K 2 CO 3 , H 2 O,85 ° C, 6 h; iii. NaClO 2 , H 2 O, 10—20 ° C, 12 h; iv. 1) SOCl 2 , DMF, CH 2 Cl 2 , 20 ° C, 1 h, 2) reflux, 15 min, 3) AlCl 3 , CH 2 Cl 2 , 20 ° C,30 min or (CF 3 CO) 2 O, CHCl 3 , molecular sieves 4 Å, 20 ° C, 18 h; v. DIBAL?H, CH 2 Cl 2 , –78 ° C, 15 min; vi. PBr 3 , PhMe, 0 ° C, 24 h;vii. NaBH 3 CN, HMPA, 70 °C, 1 h.

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