A 250 ml round bottom flask with heating mantle, magnetic stirrer and water condenser was charged with 8.0 g (0.0293 mol) 3-bromophenyl succinic acid, 3.5 g (0.0310 mol) selenium dioxide and 70 ml acetic anhydride. A rubber tube ran from the top of the water condenser to a 1 l beaker charged with 500 ml commercial Chlorox. The mixture was refluxed for 22 h, the reduced selenium dioxide salts were filtered off with a water aspirator and sintered glass funnel. The filtrate was concentrated to 40 ml on a rotovap in hot 80ºC water. Cooling in ice to 0º C gave a copious tan precipitate, which was suction filtered a sintered glass funnel under water aspirator pressure. The filtrate was washed three times with 5 ml portions of 50/50 ether/hexane. Drying in a vacuum desicator blue Drierite desicant under pump vacuum (~2 torr) for 4 h gave 4.75 g (64.2%) 4-Bromophenyl maleic anhydride, as tan crystals. The product is suitable for futher reactions at this point but still has a slight odor. Recrystalization from hot hexane yieldded 2.82g of odor free product, Other runs gave yields in the 60-70% range.

mp 152-154ºC

1H NMR: (60 Mhz, DMSO-D₆), δ 7.8 ( 2H, d, J = 9 Hz, aromatics), 7.4 ( 2H, d, J = 9 Hz, aromatics) , 7.0 (s, 1H, olefinic).

IR (CDCl₃), 1860(m), 1820(m),1800(m), 1775(vs), 1620(m), 1405(m), 1320(w), 1300(w), 1250(w), 1230(w), 1185(w), 1160(w), 1090(m), 1070(m), 1050(m), 1005(m), 820(s) cm^-1.

Richard K. Hill "A convenient Synthesis of Aryl Maleic Anhydrides", J. Org. Chem, 1961, 26(11), pp 4745-4747, DOI:10.10212/Jo0106a549 .

John H. MacMillan and Stephen S. Washburne "Further Investigation of the Interaction of Trimethylsilyl Azide with Substituted Maleic Anhydrides, Synthesis of 4-and 5-Aryl Substituted 1,3(3H) Oxazine-2,6-Diones" J.Heterocyclic Chemistry Vol. 12, p1215 (1975). DOI: 10.1002/jhet.5570120624