Dimethylformamide → 10-Bromoanthracene-9-carbaldehyde

Participants

Reaction Steps

This material was made from 9,10-dibromoanthracene (Eastman, 20 g, 60 mmol) by the procedure of R. Kuhn and H. Fischer, Chem. Ber. 94 3060 (1961) with some modifications. In this procedure, the reaction mixture was cooled to -78° before the n-BuLi (Aldrich) was added. The resulting mixture was warmed to RT over 1 h and then refluxed until the crystalline starting material disappeared. The mixture was then cooled to -78° again before the DMF was added (in one portion). The flask was warmed to RT and then quenched with 1M HBr (200 mL). The two-phase system was then extracted with CH2Cl2 (3×500 mL). The extracts were combined, dried (MgSO4), filtered, and the solvent removed to give the crude material. This was purified by preparative HPLC using PhCH3 as the eluting solvent to give 13.06 g (76%) of 10-bromo-9-anthracenecarbaldehyde mp 215°-216.5°, (lit. mp 218°, P. Kuhn and H. Fischer, Chem. Ber. 94 3060 (1961)), (C, H, Br).

Provenance & Evidence