ChemicalBook CAS DataBase List 4'-ETHYL-3'-METHYLACETANILIDE

4'-ETHYL-3'-METHYLACETANILIDE synthesis

4synthesis methods

Product Name:4'-ETHYL-3'-METHYLACETANILIDE
CAS Number:7149-81-7
Molecular formula:C11H15NO
Molecular Weight:177.24

90914-81-1
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557-20-0
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7149-81-7
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Yield:7149-81-7 98%

Reaction Conditions:

Stage #1: 4-bromo-3-methylacetanilide;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in 1,4-dioxane; for 0.333333 h;Inert atmosphere;
Stage #2: diethylzinc in 1,4-dioxane;hexane at 20 - 80; for 2.25 h;Inert atmosphere;

Steps:

1.A

To a well-stirred solution of 4-bromo-3-methylacetanilide (5.0 g, 22 mmol) in anhydrous 1 ,4-dioxane (100 mL) is added [l , l '-bis(diphenylphosphino)- ferrocene]dichloropalladium(II) (0.802 g, 1.10 mmol). This mixture is sparged with nitrogen for 20 min. and diethyl zinc in hexane (0.8 M, 60.3 mL, 48.2 mmol) is added slowly via syringe. The reaction is stirred at rt under nitrogen for 15 min. and then heated at 80 °C for 2 h. The reaction is cooled to rt, diluted with ethyl acetate (100 mL), and washed with IN HC1, water, saturated sodium bicarbonate and brine. The organic layers are dried with anhydrous sodium sulfate and concentrated. The residue is subjected to a silica gel (230-400 mesh, 50 g, elution with ethyl acetate) to give 3.80 g (98%) of N-(4- ethyl-5-methylphenyl)acetamide as a solid.

References:

WO2011/126567,2011,A1 Location in patent:Page/Page column 173-174

4433-63-0 Synthesis