Bromide ion → 6-Methoxychromone

Participants

Reaction Steps

A mixture of 6-hydroxychromone (4.5 g; 27.7 mmol), CH2Cl2 (150 ml), water (150 ml), dimethylsulphate (4 ml; 41.5 mmol), benzyltributylammmonium bromide (2 g; 5.5 mmol) and NaHCO3 (1.67 g; 41.5 mmol) was stirred for 24 hours at ambient temperature. The organic phase was decanted, washed with water, a dilute solution of ammonium hydroxide and with 1N HCl, it was dried over MgSO4 and evaporated. It was purified by chromatography, eluting with ethyl acetate/petroleum ether (50/50) to give 6-methoxychromone (4 g; 83%) as a brown solid.

Provenance & Evidence