2-chloro-3-fluoroaniline

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A solution of acetic anhydride (10 mL, 106 mmol) and formic acid (30 mL, 795 mmol) was stirred at room temperature for 10 mins. 2-Chloro-3-fluoroaniline (2.9 g, 20 mmol) was added and the reaction mixture was stirred at 60° C. for 1.5 h. After cooling to room temperature, the solvents were removed in vacuo and the residue was redissolved in DCM (100 mL) and was washed with sat aq. NaHCO3 until the aqueous phase had a measured pH of 8. The organic layer was further washed with water (2×100 mL), separated and dried over MgSO4. Filtration and concentration in vacuo gave N-(2-chloro-3-fluoro-phenyl)-formamide (3.3 g, 95%) as a colorless solid which did not require further purification. MS (M+H)+: 173.9, tR=2.04 min (method 1). After cooling to room temperature the solvents were removed in vacuo the residue was redissolved in DCM (100 mL) was washed with sat aq. NaHCO3 until the aqueous phase The organic layer was further washed with water (2×100 mL) separated dried over MgSO4 Filtration and concentration in vacuo

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

Procedure: A solution of acetic anhydride (10 mL, 106 mmol) and formic acid (30 mL, 795 mmol) was stirred at room temperature for 10 mins. 2-Chloro-3-fluoroaniline (2.9 g, 20 mmol) was added and the reaction mixture was stirred at 60° C. for 1.5 h. After cooling to room temperature, the solvents were removed in vacuo and the residue was redissolved in DCM (100 mL) and was washed with sat aq. NaHCO3 until the aqueous phase had a measured pH of 8. The organic layer was further washed with water (2×100 mL), separated and dried over MgSO4. Filtration and concentration in vacuo gave N-(2-chloro-3-fluoro-phenyl)-formamide (3.3 g, 95%) as a colorless solid which did not require further purification. MS (M+H)+: 173.9, tR=2.04 min (method 1). After cooling to room temperature the solvents were removed in vacuo the residue was redissolved in DCM (100 mL) was washed with sat aq. NaHCO3 until the aqueous phase The organic layer was further washed with water (2×100 mL) separated dried over MgSO4 Filtration and concentration in vacuo

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

Procedure: A solution of acetic anhydride (10 mL, 106 mmol) and formic acid (30 mL, 795 mmol) was stirred at room temperature for 10 mins. 2-Chloro-3-fluoroaniline (2.9 g, 20 mmol) was added and the reaction mixture was stirred at 60° C. for 1.5 h. After cooling to room temperature, the solvents were removed in vacuo and the residue was redissolved in DCM (100 mL) and was washed with sat aq. NaHCO3 until the aqueous phase had a measured pH of 8. The organic layer was further washed with water (2×100 mL), separated and dried over MgSO4. Filtration and concentration in vacuo gave N-(2-chloro-3-fluoro-phenyl)-formamide (3.3 g, 95%) as a colorless solid which did not require further purification. MS (M+H)+: 173.9, tR=2.04 min (method 1). After cooling to room temperature the solvents were removed in vacuo the residue was redissolved in DCM (100 mL) was washed with sat aq. NaHCO3 until the aqueous phase The organic layer was further washed with water (2×100 mL) separated dried over MgSO4 Filtration and concentration in vacuo

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

Procedure: Substituting 2-chloro-3-fluoroaniline as a starting material for 2,3-dichloroaniline and following the procedure of Example 1 yields 4-chloro-5-fluoro-2-indanamine.

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

Procedure: 19.6 g. of 2-chloro-3-fluoronitrobenzene (0.11 mole) is reduced with stannous chloride (118 g., 0.63 mole) in 180 ml. of concentrated hydrochloric acid. The solution is basified with aqueous sodium hydroxide and extracted with chloroform to yield 2-chloro-3-fluoroaniline. extracted with chloroform

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Substituting 2-chloro-3-fluoroaniline as a starting material for 2,3-dichloroaniline and following the procedure of Example 1 yields 4-chloro-5-fluoro-2-indanamine.

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

Procedure: 19.6 g. of 2-chloro-3-fluoronitrobenzene (0.11 mole) is reduced with stannous chloride (118 g., 0.63 mole) in 180 ml. of concentrated hydrochloric acid. The solution is basified with aqueous sodium hydroxide and extracted with chloroform to yield 2-chloro-3-fluoroaniline. extracted with chloroform

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

Procedure: To the solution of 2-bromo-3-fluoronitrobenzene (100 mg, 0.46 mmol) in ethanol (5 ml), Tin (II) chloride (520 mg, 2.3 mmol) was added. The reaction mixture was stirred at room temperature for 16 hours. The NaHCO3 (aq) was added to pH=7. Then was extracted with ethyl acetate (3x). The combined organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to give desired product (80 mg, 93%). EI-MS m/z 191 (M+). Then was extracted with ethyl acetate (3x) The combined organic layer was dried over MgSO4 filtered concentrated under reduced pressure