Thionyl Chloride → Methyl 2-amino-6-fluorobenzoate

Participants

Reaction Steps

5 g (31.6 mmol) 2-amino-6-fluorobenzoic acid are dissolved in 50 ml of methanol and combined with 7.9 ml (31.6 mmol) of a 4 M solution of HCL in 1,4-dioxane and stirred for 10 min. at ambient temperature. The reaction mixture is combined dropwise with 3.45 ml (47.4 mmol) thionyl chloride and refluxed for 3 h. Then the reaction mixture is neutralised with 150 ml of a saturated, aqueous NaHCO3 solution and extracted four times with 100 ml of ethyl acetate. The organic phase is dried with MgSO4 and the solvent is eliminated in vacuo.

Provenance & Evidence