Triphenylphosphine → Methyl 5-bromo-2-(2-thienylmethoxy)benzoate

Participants

Reaction Steps

Methyl 5-bromosalicylate [prepared by treating methyl 5-bromosalicyclic acid with methanol and sulphuric acid] (4.62 g, 20 mmol) was dissolved in THF (150 mL) and treated with thiophene methanol (2.28 g, 20 mmol) and triphenyl phosphine (10.4 g, 40 mmol). The reaction was cooled in an ice bath and treated with DEAD (6.96 g, 20 mmol). The resultant orange solution was allowed to stir at ambient temperature under argon for 18 hours. The reaction mixture was evaporated and the residue subjected to chromatography (eluant: diethyl ether/hexane) to give methyl 5-bromo-2-(2-thienylmethoxy)benzoate as a pink oil (3.6 g, 55%).

Provenance & Evidence