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ChemicalBook CAS DataBase List 4-Butylaniline
104-13-2

4-Butylaniline synthesis

11synthesis methods
-

Yield:104-13-2 70%

Reaction Conditions:

with sodium azide;trifluoroacetic acid in hexane at 40; for 4 h;Sealed tube;

Steps:

The general procedure for the C-C amination of secondary alcohols is as follows.
General procedure: A 20 ml vial equipped with a magnetic stirring bar was charged with secondary alcohols (0.3 mmol, 1 equiv.), NaN3 (0.75 mmol, 2.5 equiv.), n-hexane (1.0 ml, 0.3 M) and TFA (5.4 mmol, 18 equiv.) or a mixture of TFA (3.6 mmol,12 equiv.) and MeSO3H (1.8 mmol, 6 equiv.). The vial was sealed and stirred under air at 40 °C for 4 h. On completion, the reaction mixture was quenched by 2 M NaOH (5 m), extracted by ethyl acetate (5 × 2 m) and the combined organic phase was washed with brine and dried over Na2SO4. Then the mixture was concentrated and purified by flash chromatography on a short silica gel column.

References:

Liu, Jianzhong;Qiu, Xu;Huang, Xiaoqiang;Luo, Xiao;Zhang, Cheng;Wei, Jialiang;Pan, Jun;Liang, Yujie;Zhu, Yuchao;Qin, Qixue;Song, Song;Jiao, Ning [Nature Chemistry,2019,vol. 11,# 1,p. 71 - 77]

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