Aniline → sodium 4-methylbenzenesulfonate

Participants

Reaction Conditions

Reaction Steps

4-Cyanodiphenylamine (Takeuchi, H.; Takano, K. J. Chem. Soc. Perkin Trans. 1 1986, 611-618. 4-Cyanophenyltosylate (271 mg, 1.02 mmol), Pd(DBA)2 (11.7 mg, 0.02 mmol), DBtPF (14.5 mg, 0.03 mmol) and sodium 2,4,6-tri-t-butylphenoxide (346 mg, 1.22 mmol) were suspended in 2 mL of toluene in a screw-capped vial. The vial was sealed with a cap containing a PTFE septum and removed from the dry box. Aniline (102 μL, 1.12 mmol) was added to the reaction mixture by syringe. The vial was heated in a 110° C. oil bath for 16 hours. Over this time, a large amount of solid (presumably NaOTs) formed. The reaction was cooled to room temperature. The crude reaction was diluted with toluene (50 mL) and washed with water (50 mL, 1×) followed by brine (50 mL, 1×). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. Purified product was obtained in 82% yield after silica gel chromatography using 10% EtOAc in hexanes. 1H NMR: (CDCl3) δ 7.41 (d, J=8.7 Hz, 214), 7.33 (m, 2H) 6.08 (m, 3H), 6.96 (d, J=8.7 Hz, 2H), 6.43 (bs, 1H); 13C{1H} NMR: (CDCl3) δ 148.01, 139.64, 133.50, 129.38, 123.56, 120.87, 120.01, 114.64, 100.63.

Provenance & Evidence