Aniline → 2-Aminobiphenyl

Participants

Reaction Steps

40 mmol of an aniline derivative (III) were suspended or dissolved in a mixture of 20 ml of water, 8 ml of 10% by weight aqueous hydrochloric acid and 8 ml of a 1M solution of titanium(III) chloride in 16 ml of 10% by weight aqueous hydrochloric acid (48 mmol of HCl). To this suspension or solution were added, at room temperature, 2 mmol of the tetrafluoroborate salt of a diazonium compound (II) in small portions as a solid over a period of 10 minutes. Once the mixture thus formed had been stirred for a further 15 minutes, a solution of 4.0 g of sodium hydroxide and 4.0 g of sodium sulfite in 40 ml of water was added. The reaction mixture was extracted three times with diethyl ether and the combined organic phases were then washed with saturated sodium chloride solution and dried over sodium sulfate. After the crude product had been concentrated under reduced pressure and purified by column chromatography, the 2-aminobiphenyl was obtained as a light brown oil.

Provenance & Evidence