Hydrochloric Acid → 5-Bromo-1H-indene-1,3(2H)-dione

Participants

Reaction Steps

A solution of 4-bromo phthalic anhydride (4.15 g; 0.018 mole) in acetic anhydride (10 g) containing triethylamine (4 g) was treated at room temperature with ethyl acetoacetate (2.38 g; 0.02 mole). After 24 hrs. with stirring, crushed ice (20 g) and concentrated hydrochloric acid (10 ml) were added and the precipitated red solid filtered. Addition of a hot (70°-80° C) solution of hydrochloric acid (150 ml) in water (750 ml) to this solid resulted in decarboxylation and generation of 5-bromo indane-1,3-dione as red plates, m.p. (acetone) 152°-3° C. (Found; C, 48.04; H, 2.17; Br, 35.63; C9H5Br O2 requires C, 48.05; H, 2.24; Br, 35.52%).

Provenance & Evidence