Methanol → Methyl 5-bromosalicylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromosalicylic acid (200 g, 0.92 mol) in methanol (2 L) was added thionylchloride (440 g, 3.7 mol) at 0° C. with stirring and then allowed to reflux at 70° C. for 40 h. Excess solvent was distilled off and to the crude residue was added EtOAc (2 L). The organic layer was washed with 10% cold aqueous NaHCO3 solution (2×1 L), brine and dried. The solvent was removed under vacuum to give the title compound as a low melting point solid (190 g, 89%). TLC: PetEther/EtOAc, 7:3, Rf: 0.6

Provenance & Evidence