Benzenamine, 4-ethyl-2-methyl- synthesis
- Product Name:Benzenamine, 4-ethyl-2-methyl-
- CAS Number:71757-56-7
- Molecular formula:C9H13N
- Molecular Weight:135.21
Yield:71757-56-7 83%
Reaction Conditions:
with palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride;Cs2CO3 in tetrahydrofuran; for 5 h;Schlenk technique;Inert atmosphere;Reflux;
Steps:
62.A 4-ethyl-2-methylaniline
To a mixture of 4-bromo-2-methylaniline (1.86 g, 10 mmol), CS2CO3 (10 g, 30 mmol), and Pd(dppf)Cl2 (146 mg, 0.200 mmol) in a Schlenk tube under a N2 atmosphere was added dry THF (30 mL). To the stirred suspension was added trialkylborane (3.0 mL, 1 M in THF, 3.0 mmol) in one portion, and the mixture was refluxed for 5 h. The reaction was cooled to 0 °C and quenched by the addition of 10% aqueous NaOH and 30% aqueous H2O2. After stirring for 30 min at rt, the mixture was extracted with EtOAc. The combined organic layers were washed with aqueous FeSC^ and brine, dried over anhydrous Na2SC>4, filtered, and concentrated to dryness. The residue was purified by flash column chromatography to yield the title compound (1.1 g, 83% yield) as a white solid.
References:
WO2017/100668,2017,A1 Location in patent:Page/Page column 299
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