ChemicalBook CAS DataBase List 2-ETHYL-6-SEC-BUTYLANILINE

2-ETHYL-6-SEC-BUTYLANILINE synthesis

4synthesis methods

Product Name:2-ETHYL-6-SEC-BUTYLANILINE
CAS Number:71758-10-6
Molecular formula:C12H19N
Molecular Weight:177.29

73621-39-3
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671795-46-3
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71758-10-6
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Yield:71758-10-6 88 %

Reaction Conditions:

with triphenylphosphine;cobalt(II) chloride;sodium t-butanolate in tetrahydrofuran at 0;Catalytic behavior;Inert atmosphere;Schlenk technique;Reagent/catalyst;Solvent;Temperature;

Steps:

1-7 Example 1: Synthesis of 2-sec-butyl-6-ethylaniline

Under the protection of nitrogen, cobalt chloride (26.0mg, 0.2mmol) was added into a dry Schlenk bottle. After the gas was evacuated, anhydrous tetrahydrofuran (4mL) and phosphine ligand (62.9mg, 0.24mmol) were added, and stirred at room temperature for 0.5 h. sodium tert-butoxide (384mg, 4.0mmol) was added to the mixture, the reaction temperature was lowered to 0°C, and aniline bromide (400.0mg, 2.0mmol) and alkyl Grignard reagent (386.4mg, 2.4mmol) were added dropwise.Stirring was continued at 0°C for 6 h, and saturated ammonium chloride was added to quench the reaction.The reaction solution was extracted with ethyl acetate (4mL×4), the organic layers were combined, dried over anhydrous sodium sulfate, and concentrated to obtain aniline (311.9mg, yield 88%), the product purity can reach more than 95%.

References:

CN115010606,2022,A Location in patent:Paragraph 0041; 0062-0076