ChemicalBook CAS DataBase List N,N-DIBUTYLANILINE

N,N-DIBUTYLANILINE synthesis

13synthesis methods

Product Name:N,N-DIBUTYLANILINE
CAS Number:613-29-6
Molecular formula:C14H23N
Molecular Weight:205.34

462-06-6
415 suppliers
$10.00/5g

111-92-2 Synthesis

111-92-2
392 suppliers
$14.00/25mL

613-29-6
104 suppliers
$20.69/5g

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]

109-65-9 Synthesis