4-chloro-N-(2,2,2-trifluoroethyl)aniline

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

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

Procedure: (4-Chlorophenyl) (2,2,2-trifluoroethyl)amine (1.84 g, 8.8 mmol) and mono-t-butyl malonate (1.37 mL, 8.9 mmol) were dissolved in DCM (50 mL) and the solution cooled in an ice bath prior to portion wise addition of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (1.71 g, 8.9 mmol). After one hour the reaction was complete by TLC and was diluted with ethyl acetate and sequentially washed with 1 N NaOH, 1N HCl, and brine. The organic layer was dried with MgSO4 and concentrated under reduced pressure to give a white solid which was used without further purification. 1H NMR (300 MHz, CDCl3) δ ppm 1.40 (9H, s), 3.13 (2H, s), 4.34 (2H, q, J=8.7 Hz), 7.22 (2H, m), 7.41 (2H, m). the solution cooled in an ice bath sequentially washed with 1 N NaOH, 1N HCl, and brine The organic layer was dried with MgSO4 concentrated under reduced pressure to give a white solid which was used without further purification

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

Procedure: N-(4-Chlorophenyl)-trifluoroacetamide (2.22 g, 10 mmol) was dissolved in THF (100 mL) and treated with powdered lithium aluminum hydride (0.57 g, 15 mmol) under argon. The mixture was heated with stirring to reflux for 12 hours at which point both TLC and LC/MS analysis indicated the reaction was complete. The suspension was cooled in an ice bath prior to quenching with saturated aqueous sodium sulfate solution. The solution was dried with excess sodium sulfate and concentrated under reduced pressure to give 1.84 g of a viscous oil which was used without further purification. 1H NMR (300 MHz, CDCl3) δ ppm 3.70 (2H, dt, J=8.96, 15.81 Hz), 3.91 (1H, br s), 6.58 (2H, m), 7.13 (2H, m). The mixture was heated to reflux for 12 hours at which point both TLC and LC/MS analysis The suspension was cooled in an ice bath to quenching with saturated aqueous sodium sulfate solution The solution was dried with excess sodium sulfate concentrated under reduced pressure

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

Procedure: N-(4-Chlorophenyl)-trifluoroacetamide (2.22 g, 10 mmol) was dissolved in THF (100 mL) and treated with powdered lithium aluminum hydride (0.57 g, 15 mmol) under argon. The mixture was heated with stirring to reflux for 12 hours at which point both TLC and LC/MS analysis indicated the reaction was complete. The suspension was cooled in an ice bath prior to quenching with saturated aqueous sodium sulfate solution. The solution was dried with excess sodium sulfate and concentrated under reduced pressure to give 1.84 g of a viscous oil which was used without further purification. 1H NMR (300 MHz, CDCl3) δ ppm 3.70 (2H, dt, J=8.96, 15.81 Hz), 3.91 (1H, br s), 6.58 (2H, m), 7.13 (2H, m). The mixture was heated to reflux for 12 hours at which point both TLC and LC/MS analysis The suspension was cooled in an ice bath to quenching with saturated aqueous sodium sulfate solution The solution was dried with excess sodium sulfate concentrated under reduced pressure

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

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

Procedure: (4-Chlorophenyl) (2,2,2-trifluoroethyl)amine (1.84 g, 8.8 mmol) and mono-t-butyl malonate (1.37 mL, 8.9 mmol) were dissolved in DCM (50 mL) and the solution cooled in an ice bath prior to portion wise addition of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (1.71 g, 8.9 mmol). After one hour the reaction was complete by TLC and was diluted with ethyl acetate and sequentially washed with 1 N NaOH, 1N HCl, and brine. The organic layer was dried with MgSO4 and concentrated under reduced pressure to give a white solid which was used without further purification. 1H NMR (300 MHz, CDCl3) δ ppm 1.40 (9H, s), 3.13 (2H, s), 4.34 (2H, q, J=8.7 Hz), 7.22 (2H, m), 7.41 (2H, m). the solution cooled in an ice bath sequentially washed with 1 N NaOH, 1N HCl, and brine The organic layer was dried with MgSO4 concentrated under reduced pressure to give a white solid which was used without further purification

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

Procedure: N-(4-Chlorophenyl)-trifluoroacetamide (2.22 g, 10 mmol) was dissolved in THF (100 mL) and treated with powdered lithium aluminum hydride (0.57 g, 15 mmol) under argon. The mixture was heated with stirring to reflux for 12 hours at which point both TLC and LC/MS analysis indicated the reaction was complete. The suspension was cooled in an ice bath prior to quenching with saturated aqueous sodium sulfate solution. The solution was dried with excess sodium sulfate and concentrated under reduced pressure to give 1.84 g of a viscous oil which was used without further purification. 1H NMR (300 MHz, CDCl3) δ ppm 3.70 (2H, dt, J=8.96, 15.81 Hz), 3.91 (1H, br s), 6.58 (2H, m), 7.13 (2H, m). The mixture was heated to reflux for 12 hours at which point both TLC and LC/MS analysis The suspension was cooled in an ice bath to quenching with saturated aqueous sodium sulfate solution The solution was dried with excess sodium sulfate concentrated under reduced pressure