Dimethylformamide → 10-Bromoanthracene-9-carbaldehyde

Participants

Reaction Steps

To the yellow suspension of 9,10-Dibromoanthracene (2 g, 5.95 mmol) in THF (20 mL) at −90° C., n-BuLi (2.88 mL, 7.18 mmol, 2.5 M in hexane) was added dropwise. Orange solution was observed after 45 min additional stirring. Anhydrous DMF (0.92 mL, 11.9 mmol) was added to the orange solution. The reaction mixture was slowly warmed to room temp and stirred overnight. The reaction mixture was quenched with H2O and extracted with CH2Cl2. The organic layer was washed with 10% aq. Na2CO3 solution (3×50 mL). The CH2Cl2 layer was separated, dried over anhydrous Na2SO4, filtered and removed in vacuo to give yellow solid. The crude product was purified by column chromatography using 30% CH2Cl2/hexane to give 6 in 68% yield. R1=0.3 (30% CH2Cl2/hexane; 1H NMR (CDCl3) δ 11.39 (s, 1H), 8.77-8.82 (d, 2H), 8.55-8.60 (d, 2H), 7.56-7.67 (m, 4H). (Ref. de Montigny, Frederic; Argouarch, Gilles; Lapinte, Claude. New route to unsymmetrical 9,10-disubstituted ethynylanthracene derivatives. Synthesis, 2006, 2, 293-298.)

Provenance & Evidence