Potassium Carbonate → 9-Bromomethylanthracene

Participants

Reaction Conditions

Reaction Steps

To a stirring suspension of 9-anthracenemethanol (2.0 g, 9.6 mmol) at 0° C. in toluene (100 ml) was added PBr3 (1.2 mL, 12.51 mmol) and the suspension was stirred at 0° C. for 1 h. The reaction mixture was then brought up to room temperature and let to stir for further 1 h. The mixture turned into a yellow solution. K2CO3 (10 mL) was added to quench the reaction. Toluene was evaporated off in-vacuo. The residue was taken up in EtOAc and washed with saturated aqueous K2CO3, water and brine and dried (MgSO4). The solvent was evaporated off in-vacuo and the crude residue was purified by flash chromatography, eluting with hexane:EtOAc (2:1) to give 47 (1.4 g, 54%) as yellow solid. H1 NMR (500 MHz, CDCl3): δ=8.45 (1H, s, Ar-10H), 8.27 (2H, d, Ar-1, 8H), 8.00 (2H, d, Ar-4, 6H), 7.62 (2H, d, Ar-2, 7H), 7.48 (2H, d, Ar-3, H), 5.50 (2H, s, CH2).

Provenance & Evidence