Methyl 3,4-Dimethoxybenzoate → Methyl 2-bromo-4,5-dimethoxybenzoate

Participants

Reaction Steps

To 10.00 g (51 mmol) of methyl 3,4 dimethoxybenzoate (6) in 50 mL of AcOH at 0° C. was added 8.90 g (56 mmol) of Br2 in 50 mL of AcOH over 1.5 h. The ice bath was removed and the mixture stirred 45 min. The reaction was quenched by pouring into 700 mL of H2O, stirred 30 min, left quiescent for 1 h, and filtered. The collected solid was washed with H2O and washed with sat. aq. Na2S2O3. The solid was partially dried, dissolved in 300 mL hot MeOH, and the resultant solution was cooled. The cool methanolic solution of product was treated with 200 mL of H2O and the white solid filtered to give 8.92 g (64% yield) of methyl-2-bromo-4,5-dimethoxybenzoate (7) as a white powder. The compound matched the physical and spectral properties of the known compound.

Provenance & Evidence