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4-Chloro-2-phenylbutyronitrile synthesis
- Product Name:4-Chloro-2-phenylbutyronitrile
- CAS Number:93273-13-3
- Molecular formula:C10H10ClN
- Molecular Weight:179.65
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Yield:93273-13-3 76%
Reaction Conditions:
with potassium carbonate in methanol;water at 0; for 3.5 h;
Steps:
4-chloro-2-phenylbutanenitrile
To a stirred solution of ethyl 4-chloro-2-cyano-2-phenylbutanoate (7.25 g, 28.8 mmol) in methanol (40 ml.) was added a half-saturated aqueous solution of potassium carbonate (8 ml.) at 0 °C and the mixture was stirred at 0 °C for 3.5 h. Hydrochloric acid was added until pH 3 was reached, then an aqueous solution of sodium bicarbonate was added until pH 7 was reached and the mixture was extracted with MTBE. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate), filtered and the solvent was removed in vacuum. Silicagel chromatography gave 3.95 g (76 % yield) of the title compound. (1011) LC-MS (Method 1): Rt = 1.15 min; MS (ESIpos): m/z = 221 / 223 [M+CH3CO]+ (1012) 1H NMR (400 MHz, DMSO-cfe) d ppm: 2.22 - 2.33 (m, 1 H), 2.42 (ddt, 1 H), 3.57 - 3.72 (m, 2 H), 4.36 (dd, 1 H), 7.32 - 7.50 (m, 4 H).
References:
WO2020/161257,2020,A1 Location in patent:Page/Page column 108; 109
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