1-(4-fluorophenyl)-N-phenylmethanimine

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

Procedure: To potassium t-butoxide (1.5 g, 13.4 mmol) in DMF (15 mL) at 75° C. was added as quickly as possible and all at once [(4-fluorophenyl)methyl]-1-H-benzotriazole (1.14 g, 5 mmol) and (4-fluorophenyl)methylenebenzenamine (1.00 g, 5 mmol) dissolved in DMF (10 mL). Within a minute the solution is poured into ice-cold water (75 mL) crystallizing the title compound which was filtered and then chromatographed (PE). The acetylene 0.54 g (50%) recrystallizes as needles: mp 95°-96° C. (MeOH); (lit.1 94°-95° C.). crystallizing the title compound which was filtered chromatographed (PE) The acetylene 0.54 g (50%) recrystallizes as needles (lit.1 94°-95° C.)

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

Procedure: To 4-fluorobenzaldehyde (24.8 g, 0.200 mol) and aniline (18.6 g, 0.200 mol) was added benzene (200 mL) and acetic acid (0.7 mL) and the mixture is heated under reflux until all the water (3.6 mL) was azeotropically removed. The solvent is evaporated and the residual oil upon cooling and stirring crystallized. The white mass was then recrystallize as needles (28 g, 70%): mp 39°-40° C. (PE) (lit.1 mp 40° C.). the mixture is heated was azeotropically removed The solvent is evaporated the residual oil upon cooling crystallized The white mass was then recrystallize as needles (28 g, 70%)

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

Procedure: To 4-fluorobenzaldehyde (24.8 g, 0.200 mol) and aniline (18.6 g, 0.200 mol) was added benzene (200 mL) and acetic acid (0.7 mL) and the mixture is heated under reflux until all the water (3.6 mL) was azeotropically removed. The solvent is evaporated and the residual oil upon cooling and stirring crystallized. The white mass was then recrystallize as needles (28 g, 70%): mp 39°-40° C. (PE) (lit.1 mp 40° C.). the mixture is heated was azeotropically removed The solvent is evaporated the residual oil upon cooling crystallized The white mass was then recrystallize as needles (28 g, 70%)

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

Procedure: To potassium t-butoxide (1.5 g, 13.4 mmol) in DMF (15 mL) at 75° C. was added as quickly as possible and all at once [(4-fluorophenyl)methyl]-1H-benzotriazole (1.14 g, 5 mmol) and (4-fluorophenyl)methylenebenzenamine (1.00 g, 5 mmol) dissolved in DMF (10 mL). Within a minute the solution is poured into ice-cold water (75 mL) crystallizing the title compound which was filtered and then chromatographed (PE). The acetylene 0.54 g (50%) recrystallizes as needles: mp 95°-96° C. (MeOH); (lit.1 94°-95° C.). crystallizing the title compound which was filtered chromatographed (PE) The acetylene 0.54 g (50%) recrystallizes as needles (lit.1 94°-95° C.)

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

Procedure: To 4-fluorobenzaldehyde (24.8 g, 0.200 mol) and aniline (18.6 g, 0.200 mol) was added benzene (200 mL) and acetic acid (0.7 mL) and the mixture is heated under reflux until all the water (3.6 mL) was azeotropically removed. The solvent is evaporated and the residual oil upon cooling and stirring crystallized. The white mass was then recrystallized as needles (28 g, 70%): mp 39°-40° C. (PE) (lit.1 mp 40° C.). the mixture is heated was azeotropically removed The solvent is evaporated the residual oil upon cooling crystallized The white mass was then recrystallized as needles (28 g, 70%)