5-bromo-6-fluoro-1,3-dihydroindol-2-one

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 250 mL round bottom flask was added ethyl 2-(5-bromo-4-fluoro-2-nitrophenyl)acetate (5.2 g, 17 mmol), iron (4.7 g, 85 mmol) and 50 mL of AcOH. The reaction mixture was heated at 60° C. for 1 hour. The reaction mixture was then concentrated, dissolved in 100 mL of EtOAc, filtered, and washed with 50 mL of a saturated NaHCO3 solution. The organic layer was concentrated and purified with silica gel column chromatography, eluting with 40% EtOAc/hexane to give 5-bromo-6-fluoroindolin-2-one (3.4 g, 87% yield) as a white solid. MS m/z: 230 (M+1). 1H NMR (400 MHz, CD3OD) δ ppm 3.49-3.54 (m, 2H), 6.77 (d, J=8.80 Hz, 1H), 7.45 (d, J=6.65 Hz, 1H). The reaction mixture was then concentrated dissolved in 100 mL of EtOAc filtered washed with 50 mL of a saturated NaHCO3 solution The organic layer was concentrated purified with silica gel column chromatography eluting with 40% EtOAc/hexane

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 250 mL round bottom flask was added ethyl 2-(5-bromo-4-fluoro-2-nitrophenyl)acetate (5.2 g, 17 mmol), iron (4.7 g, 85 mmol) and 50 mL of AcOH. The reaction mixture was heated at 60° C. for 1 hour. The reaction mixture was then concentrated, dissolved in 100 mL of EtOAc, filtered, and washed with 50 mL of a saturated NaHCO3 solution. The organic layer was concentrated and purified with silica gel column chromatography, eluting with 40% EtOAc/hexane to give 5-bromo-6-fluoroindolin-2-one (3.4 g, 87% yield) as a white solid. MS m/z: 230 (M+1). 1H NMR (400 MHz, CD3OD) δ ppm 3.49-3.54 (m, 2H), 6.77 (d, J=8.80 Hz, 1H), 7.45 (d, J=6.65 Hz, 1H). The reaction mixture was then concentrated dissolved in 100 mL of EtOAc filtered washed with 50 mL of a saturated NaHCO3 solution The organic layer was concentrated purified with silica gel column chromatography eluting with 40% EtOAc/hexane

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 250 mL round bottom flask was added ethyl 2-(5-bromo-4-fluoro-2-nitrophenyl)acetate (5.2 g, 17 mmol), iron (4.7 g, 85 mmol) and 50 mL of AcOH. The reaction mixture was heated at 60° C. for 1 hour. The reaction mixture was then concentrated, dissolved in 100 mL of EtOAc, filtered, and washed with 50 mL of a saturated NaHCO3 solution. The organic layer was concentrated and purified with silica gel column chromatography, eluting with 40% EtOAc/hexane to give 5-bromo-6-fluoroindolin-2-one (3.4 g, 87% yield) as a white solid. MS m/z: 230 (M+1). 1H NMR (400 MHz, CD3OD) δ ppm 3.49-3.54 (m, 2H), 6.77 (d, J=8.80 Hz, 1H), 7.45 (d, J=6.65 Hz, 1H). The reaction mixture was then concentrated dissolved in 100 mL of EtOAc filtered washed with 50 mL of a saturated NaHCO3 solution The organic layer was concentrated purified with silica gel column chromatography eluting with 40% EtOAc/hexane

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 250 mL round bottom flask was added ethyl 2-(5-bromo-4-fluoro-2-nitrophenyl)acetate (5.2 g, 17 mmol), iron (4.7 g, 85 mmol) and 50 mL of AcOH. The reaction mixture was heated at 60° C. for 1 hour. The reaction mixture was then concentrated, dissolved in 100 mL of EtOAc, filtered, and washed with 50 mL of a saturated NaHCO3 solution. The organic layer was concentrated and purified with silica gel column chromatography, eluting with 40% EtOAc/hexane to give 5-bromo-6-fluoroindolin-2-one (3.4 g, 87% yield) as a white solid. MS m/z: 230 (M+1). 1H NMR (400 MHz, CD3OD) δ ppm 3.49-3.54 (m, 2H), 6.77 (d, J=8.80 Hz, 1H), 7.45 (d, J=6.65 Hz, 1H). The reaction mixture was then concentrated dissolved in 100 mL of EtOAc filtered washed with 50 mL of a saturated NaHCO3 solution The organic layer was concentrated purified with silica gel column chromatography eluting with 40% EtOAc/hexane