methyl 4-amino-2-chloro-6-fluorobenzoate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of methyl 4-(tert-butoxycarbonylamino)-2-chloro-6-fluoro-benzoate (6.53 g, 21.5 mmol) in dichloromethane (40 mL) was added TFA (9.94 mL). The mixture was stirred at room temperature for 4 hours. The mixture was then concentrated. Water (30 mL) was added to the residue, and pH was adjusted 10 with 25% NaOH. The resulting suspension was extracted with EtOAc (3×). The combined organics were dried (Na2SO4), filtered and concentrated to give the title compound (4.41 g, quantitative yield) as an off-white solid. 1H NMR (400 MHz, CD2Cl2) δ 6.54 (s, 1H), 6.34 (dd, J=11.6, 2.1 Hz, 1H), 4.19 (s, 2H), 3.90 (s, 3H). LCMS (ESI) m/z 204.0 [M+H+]. The mixture was then concentrated Water (30 mL) was added to the residue, and pH The resulting suspension was extracted with EtOAc (3×) The combined organics were dried (Na2SO4) filtered concentrated