Abstract
Hydrolysis and bromination of phthalic anhydride in water gave a mixture of the monosodium salt of 4-bromo-phthalic acid. These were reacted with phenylacetylene under Sonogashira coupling reaction conditions in an aqueous medium. Acidification afforded 4-phenylethynylphthalic acid and then dehydration of this gave 4-phenylethynylphthalic anhydride in 76% overall yield. Compared with traditional synthetic methods, this method has the advantage of low cost, convenient manipulation and is environmentally friendly.
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References
1.
Feger C.
,
Khohasteh M.M.
, and
McGrath J.E.
, Polyimides: chemistry, materials, and characterization , Elsevier , Amsterdam , 1989 .
2.
Ghosh M.K.
, and
Mittal K.L.
, Polymides: fundamentals and applications , Marcel Dekker , New York , 1996 .
3.
Hergenrother P.M.
, and
Smith J.G. Jr
, Polymer , 1994 , 35 , 4857 .
4.
Hergenrother P.M.
, and
Smith J.G. Jr
, US 5567800, 1996 .
5.
Takekoshi T.
, and
Terry J.M.
, Polymer , 1994 , 35 , 4874 .
6.
Johnston J.A.
,
Li F.M.
, and
Harris F.W.
, Polymer , 1994 , 35 , 4865 .
7.
Meyer G.W.
,
Tan B.
, and
McGrath J.E.
, High Perform. Polym. , 1994 , 6 , 423 .
8.
Oren J.
, IL 115814, 1999 .
9.
Gould K.J.
,
Hacker N.P.
,
McOmie J.F.W.
, and
Perry D.H.
, J. Chem. Soc., Perkin Trans. 1 , 1980 , 8 , 1834 .
10.
Urazoe D.
,
Mori H.
, and
Yamakawa K.
, US 20050215820, 2005 .
11.
Akira I.
,
Yoshihiro N.
, and
Osamu U.
, JP 2010070527A, 2010 .
12.
Zon J.
,
Misiak P.
,
Amrhein N.
, and
Gancarz R.
, Chem. Biodiversity , 2005 , 2 , 1187 .
13.
Sabourin E.T.
, and
Onopchenko A.
, J. Org. Chem. , 1983 , 48 , 5135 .
14.
Wu T.F.
,
Yang M.J.
,
Wang Y.
,
Gao G.W.
, and
Men J.
, Chin. Chem. Lett. , 2011 , 22 , 159 .
15.
Amatore C.
,
Blart E.
,
Genêt J.P.
,
Jutand A.
,
Lemaire-Audoire S.
, and
Savignac M.
, J. Org. Chem. , 1995 , 60 , 6829 .
16.
Chen H.
,
Liu H.C.
, and
Li X.J.
, J. Mol. Catal. (China) , 1994 , 8 , 124 .
17.
Lin M.J.
,
Wang J.D.
,
Chen N. S
, and
Huang J.H.
, J. Coord. Chem. , 2006 , 59 , 607 .