1-(5-broMopyridin-3-yl)-2,2,2-trifluoroethanol

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

Procedure: The general procedure B using 51.7 mg (0.215 mmol) of o-tolyltriflate and 29.4 μl (0.323 mmol) of aniline gave 95% yield of N-(2-methylphenyl)aniline after sublimation (130° C., 0.1 torr).

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

Procedure: The general procedure B using 51.7 mg (0.215 mmol) of o-tolyltriflate and 29.4 μl (0.323 mmol) of aniline gave 95% yield of N-(2-methylphenyl)aniline after sublimation (130° C., 0.1 torr).

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

Procedure: 2-Bromotoluene (2 mmol) is heated to 230° C. for 6 hours with aniline (20 mmol) in the presence of [(C6H5)2PCH2]2Ni(CO)2 (0.2 mmol) using ethanol (1.2 mL) as the solvent in a sealed tube to form 2-anilinotoluene. 2-Anilinotoluene is oxidized with potassium permaganate in water to form 2-anilinobenzoic acid. (See Cramer, et al., J. Org. Chem. (1975), 40:2267).

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

Procedure: The general procedure B using 51.7 mg (0.215 mmol) of o-tolyltriflate and 29.4 μl (0.323 mmol) of aniline gave 95% yield of N-(2-methylphenyl)aniline after sublimation (130° C., 0.1 torr).