1-(4-chlorophenyl)-1-phenylhydrazine

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

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

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenylhydrazine (1.2 equiv., 0.6 mmol, 0.06 mL), 4-chlorobromobenzene (1.0 equiv., 0.5 mmol, 96 mg), Pd(OAc)2 (0.05 equiv., 0.025 mmol, 6 mg), BINAP (0.05 equiv., 0.025 mmol, 16 mg), NaOtBu (1.4 equiv., 0.7 mmol, 67 mug) and dilsopropylamine (2 mL) were added to an oven dried test tube which was capped with a septum and purged briefly with argon (˜1 min.), and then heated to 80° C. under argon for 2.5 hours. The reaction was then cooled to room temperature, diluted with Et2O (2 mL), filtered through Celite and concentrated under vacuum. The crude mixture was purified by flash column chromatography (10% EtOAc/Hex) to give the title product as a yellow oil (42 mg, 0.19 mmol, 39% yield). dried test tube which was capped with a septum purged briefly with argon (˜1 min.) The reaction was then cooled to room temperature diluted with Et2O (2 mL) filtered through Celite concentrated under vacuum The crude mixture was purified by flash column chromatography (10% EtOAc/Hex)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenylhydrazine (1.2 equiv., 0.6 mmol, 0.06 mL), 4-chlorobromobenzene (1.0 equiv., 0.5 mmol, 96 mg), Pd(OAc)2 (0.05 equiv., 0.025 mmol, 6 mg), BINAP (0.05 equiv., 0.025 mmol, 16 mg), NaOtBu (1.4 equiv., 0.7 mmol, 67 mug) and dilsopropylamine (2 mL) were added to an oven dried test tube which was capped with a septum and purged briefly with argon (˜1 min.), and then heated to 80° C. under argon for 2.5 hours. The reaction was then cooled to room temperature, diluted with Et2O (2 mL), filtered through Celite and concentrated under vacuum. The crude mixture was purified by flash column chromatography (10% EtOAc/Hex) to give the title product as a yellow oil (42 mg, 0.19 mmol, 39% yield). dried test tube which was capped with a septum purged briefly with argon (˜1 min.) The reaction was then cooled to room temperature diluted with Et2O (2 mL) filtered through Celite concentrated under vacuum The crude mixture was purified by flash column chromatography (10% EtOAc/Hex)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenylhydrazine (1.2 equiv., 0.6 mmol, 0.06 mL), 4-chlorobromobenzene (1.0 equiv., 0.5 mmol, 96 mg), Pd(OAc)2 (0.05 equiv., 0.025 mmol, 6 mg), BINAP (0.05 equiv., 0.025 mmol, 16 mg), NaOtBu (1.4 equiv., 0.7 mmol, 67 mug) and dilsopropylamine (2 mL) were added to an oven dried test tube which was capped with a septum and purged briefly with argon (˜1 min.), and then heated to 80° C. under argon for 2.5 hours. The reaction was then cooled to room temperature, diluted with Et2O (2 mL), filtered through Celite and concentrated under vacuum. The crude mixture was purified by flash column chromatography (10% EtOAc/Hex) to give the title product as a yellow oil (42 mg, 0.19 mmol, 39% yield). dried test tube which was capped with a septum purged briefly with argon (˜1 min.) The reaction was then cooled to room temperature diluted with Et2O (2 mL) filtered through Celite concentrated under vacuum The crude mixture was purified by flash column chromatography (10% EtOAc/Hex)