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ChemicalBook CAS DataBase List N,N-DIBUTYLANILINE
613-29-6

N,N-DIBUTYLANILINE synthesis

13synthesis methods
-

Yield: 82%

Reaction Conditions:

Stage #1:dibutylamine with n-butyllithium in tetrahydrofuran;hexane at 25; for 0.166667 h;Inert atmosphere;
Stage #2:fluorobenzene in tetrahydrofuran;hexane at 25; for 0.5 h;Inert atmosphere;

Steps:

General procedure for the synthesis of target compounds 3
General procedure: To an oven-dried round-bottom flask with a stir bar were charged with a solution of secondary amines 2 (1.5 mmol) in 1 mLdry THF at room temperature under an argon atmosphere. To thissolution was slowly added 1.2 mL nBuLi (2.5 mol/L in n-hexane,3.0 mmol) via syringe. After stirring at 25 C for 10 min, a solution of fluoroarene 1 (1.0 mmol) in 1mL dry THF was added to the reaction flask. The reaction mixture was stirred for 0.5 h at 25 C, and then quenched with 2 mL saturated aqueous solution of NaCl and extracted with H2O (20 mL) and ethyl acetate (3 20 mL). The organic layer was separated and dried with anhydrous Na2SO4, filtered, and evaporated under vacuum. The crude product was purified by column chromatography on silica gel using a petroleum ether/ethyl acetate mixture as eluent to afford the pure target compounds.

References:

Lin, Yingyin;Li, Meng;Ji, Xinfei;Wu, Jingjing;Cao, Song [Tetrahedron,2017,vol. 73,# 11,p. 1466 - 1472]

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