As a common heterocyclic compound, it belongs to copper-catalyst compound, name is Copper(I) bromide, and cas is 7787-70-4, its synthesis route is as follows.
a. 2-(carboxy-5-nitro-phenyl)malonic acid dimethyl ester (2) A solution of 2-chloro-4-nitrobenzoic acid (75g, 372mmol) in dimethyl malonate (900mL) was sparged with nitrogen for 15 min. Sodium methoxide (48.3g, 894mmol) was added in one portion and the contents exothermed to 48C. Fifteen minutes later, copper (I) bromide (5.4g, 37mmol) was added in one portion and the contents heated to 70C for 24 hrs. The reaction was 70% complete by nmr, the contents heated to 85C for 5 hrs to completely consume the 2-chloro-4-nitrobenzoic. Water (900mL) was added to the cooled reaction followed by hexanes (900mL). The aqueous layer was separated, toluene (900mL) added, filtered through celite, and aqueous layer separated. Fresh toluene (1800mL) was added to the aqueous layer and the biphasic mixture acidified with 6N aqueous HCl (90mL). A white precipitate formed and the contents stirred for 18 hrs. The product was filtered off and dried to give a white solid (78.1g, 70%) mp=153C. 1H NMR (CD3)2SO delta 8.37 (d, J = 2 Hz, 1H), 8.30 (d, J = 1Hz, 2H), 5.82 (s, 1H), 3.83 (s, 6H). 13C NMR (CD3)2SO delta 168.0, 167.3, 149.4, 137.1, 135.8, 132.5, 125.4, 123.7, 54.5, 53.4. Anal. Calcd for C11H10NO8: C, 48.49; H, 3.73; N, 4.71. Found: C, 48.27; H, 3.72; N, 4.76.
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Reference£º
Patent; PFIZER INC.; EP1181954; (2002); A2;,
Copper catalysis in organic synthesis – NCBI
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”