ChemicalBook CAS DataBase List 3-(2',4'-DICHLOROPHENYL)-3-OXOPROPANENITRILE

3-(2',4'-DICHLOROPHENYL)-3-OXOPROPANENITRILE synthesis

6synthesis methods

Product Name:3-(2',4'-DICHLOROPHENYL)-3-OXOPROPANENITRILE
CAS Number:39528-61-5
Molecular formula:C9H5Cl2NO
Molecular Weight:214.05

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3-(2',4'-DICHLOROPHENYL)-3-OXOPROPANENITRILE

39528-61-5
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Yield:39528-61-5 98%

Reaction Conditions:

Stage #1: acetonitrilewith n-butyllithium in tetrahydrofuran;hexane at -78; for 0.25 h;
Stage #2: 2,4-dichlorobenzoyl chloride in tetrahydrofuran;hexane; for 0.666667 h;

Steps:

1.1

To a stirred solution of acetonitrile (2.0 mL, 38.2 mmol) in THF (50 mL) at -78° C. was added ⁿBuLi (1.81 M in hexane, 16 mL, 28.7 mmol). The resulting slurry was kept at -78° C. for 15 min and 2,4-dichlorobenzoyl chloride (2.0 g, 9.55 mmol) was added dropwise to the acetonitrile anion. After 40 min, the reaction was quenched by addition of saturated NH₄Cl (30 mL). THF was removed under reduced pressure and the suspension was filtered. The solid was washed with H₂O (100 mL) and dried to give 3-(2,4-dichlorophenyl)-3-oxopropanenitrile (2.0 g, 98%, >95% purity) as a light yellow solid. ¹H NMR (400 MHz, CDCl₃) 7.64 (d, J=8.32 Hz, 1H), 7.52 (d, J=1.76 Hz, 1H), 7.41 (dd, J=1.76, 8.32 Hz, 1H), 4.13 (s, 2H).

References:

US2006/142576,2006,A1 Location in patent:Page/Page column 16-17