Abstract
10% mol SmI3 catalysed the Friedel–Crafts acylation of aromatic ethers by acyl chlorides in acetonitrile with the yields of 48–82%. Reactions of various substituted aromatic ethers with acyl chloride were studied. The structures of compounds were established by IR and 1H NMR. The main product obtained with anisole is the para-substituted compound with only a trace (<5 %) of meta and ortho substituted products. This shows that the acylation of aromatic ethers is highly regioselective in the presence of SmI3, a pattern repeated with the other aromatic ethers used.
References
1.
Girard P.
,
Namy J. L.
, and
Kagan H. B.
, J. Am. Chem. Soc. , 1980 , 102 , 2693 .
2.
Molander G.A.
, and
Harris C. R.
, Chem. Rev. , 1996 , 96 , 307 .
3.
Concellon J.M.
,
Rodriguez-Solla H.
, and
Llavona R.
, J. Org. Chem. , 2003 , 68 , 1132 .
4.
Talukdar S.
, and
Fang J. M.
, J. Org. Chem. , 2001 , 66 , 330 .
5.
Howell D. M.
,
Barker S. M.
,
Watson F. C.
,
Light M. E.
,
Hursthouse M. B.
, and
Kilburn J. D.
, Org. Lett. , 2004 , 6 , 1943 .
6.
Ricci M.
,
Blakskjar P.
, and
Skrydstrup T.
, J. Am. Chem. Soc. , 2000 , 122 , 2413 .
7.
Concellon J.M.
, and
Huerta M.
, Tetrahedron Lett. , 2003 , 44 , 1931 .
8.
Liao P.H.
,
Huang Y.
, and
Zhang Y. M.
, Synth. Commun. , 1997 , 27 , 1483 .
9.
Zhang Y.M.
, and
Liu Y. K.
, Chin. J. Org. Chem. , 2001 , 21 , 962 .
10.
Bao W.L.
,
Yin T. K.
,
Zhang Y. M.
, and
Yu M. X.
, Org. Prep. Proc. Int. , 1997 , 3 , 335 .
11.
Yu M.X.
,
Zhang Y. M.
, and
Bao W. L.
, Chin. J. Chem. , 1999 , 17 , 4 .
12.
Wang X.X.
, and
Zhang Y. M.
, Indian J. Chem. Section B, 2003 , 42 , 2632 .
13.
Zhang X.L.
, and
Zhang Y. M.
, Synth. Commun. , 2002 , 33 , 161 .
14.
Wu H.Y.
,
Ding J. C.
, and
Liu Y. K.
, J. Indian Chem. Soc. , 2003 , 80 , 36 .
15.
Zhong W.H.
, and
Zhang Y. M.
, Chin. J. Org. Chem. , 2000 , 20 , 747 .
16.
Furniss B.S.
,
Hannaford A. J.
,
Smith P. W. G.
, and
Tatchell A. R.
,
Vogels
“Textbook of Practical Organic Chemistry,” 5th ed. England : Addison Wesley Longman Limited , 1989 , 1006 .
17.
Metivier P.
, in “Fine Chemicals through Heterogeneous Catalysis” (
Sheldon R. A.
, and
van Bekkum H.
, Eds.), Wiley– VCH , Weinheim , 2001 , 161 .
18.
Hachiya L.
,
Moriwaki M.
, and
Kobayashi S.
, Tetrahedron Lett. , 1995 , 36 , 409 .
19.
Repichet S.
,
Le Roux C.
,
Dubac J.
, and
Desmurs J. R.
, Eur. J. Org. Chem. , 1998 , 12 , 2743 .
20.
(a) Beilstein's Handbuch der Organichen Chemie , Vier auflage, 8 , 87 ; (b) Beilstein's Handbuch der Organichen Chemie , Vier auflage, 8 ,103; (c) Beilstein's Handbuch der Organichen Chemie , Vier auflage, 8 ,159; (d) Beilstein's Handbuch der Organichen Chemie , Vier auflage, 8 , 267; (e) Dictionary of Organic Compounds , 6th edn,
Cadogan J.I. G.
,
Ley S. V.
, and
Pattenden G.
(eds), London, 1996 , Vol. 3, 2467; (f) Dictionary of Organic Compounds , 6th edn, J.I.G. Cadogan, S.V. Ley and G. Pattenden (eds), London, 1996, Vol. 3, 2370.
21.
Ranu B.C.
,
Ghosh K.
,
Jana U.
, J. Org. Chem. , 1996 , 26 , 9546 ; (h) Dictionary of Organic Compounds , 6th edn.,
Cadogan J.I. G.
,
Ley S. V.
, and
Pattenden G.
(eds), London, 1996, Vol. 3, 2467; (i) Dictionary of Organic Compounds , 6th edn., J.I.G. Cadogan, S.V. Ley and G. Pattenden (eds), London, 1996, Vol. 3, 2370; (j) Dictionary of Organic Compounds , 6th edn., J.I.G. Cadogan, S.V. Ley and G. Pattenden (eds), London, 1996, Vol. 4, 3681.
22.
Bachelet J.P.
,
Demerseman P.
, and
Royer R.
, Bull. Soc. Chim. Fr. 1974 , 11 , 2631 .
23.
Buu-Hoi N.P.
,
Royer R.
, and
Eckert B.
, J. Org. Chem. ; 1952 , 11 , 1463 .
24.
Turaeva M.K.
,
Aknmedor K. N.
, and
Abdurasuleva A. R.
, Deposited Doc. 1976 , VINITI 3010-76, 9.
