................DR ANTHONY MELVIN CRASTO Ph.D ( ICT, Mumbai) , INDIA 25Yrs Exp. in the feld of Organic Chemistry,Working for GLENMARK GENERICS at Navi Mumbai, INDIA. Serving chemists around the world. Helping them with websites on Chemistry.Million hits on google, world acclamation from industry, academia, drug authorities for websites, blogs and educational contribution
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Thursday, 16 February 2017
cas 1192875-03-8, 181.59
C9 H5 Cl F N
2-Propenenitrile, 3-chloro-3-(3-fluorophenyl)-, (2Z)-
IV V VI II
Synthesis of (Z)-3-Chloro-3-(3-fluorophenyl)-acrylonitrile from 3'-Fluoroacetophenone.
To a solution of 3'-fluoroacetophenone (80.0 g, 0.579 mol) in 7V,N-dimethyl formamide (560 ml) at about 400C was added phosphoryl chloride (92.50 ml, 1.01 mol) dropwise, maintaining the temperature at about 39-410C during the addition. The resulting reaction mixture was stirred at about 400C overnight before sampling for conversion to 2 by HPLC.
To the resulting reaction mixture was added a solution of hydroxylamine hydrochloride (45.17 g, 0.637 mol) in 7V,N-dimethyl formamide (240 ml) dropwise, maintaining the temperature at about 39-45°C during the addition, followed by a line -wash of JV,Λ/-dimethyl formamide (40 ml). After stirring at about 400C for 15 min, the reaction mixture was sampled for conversion to 4 before cooling to about 15-200C and addition of water (800 ml) dropwise, maintaining the temperature between about 17 to about 210C. The reaction mixture was then cooled to about 5°C and held at this temperature for a further 20 min before filtration of the solid, displacement washing with two separate portions of water (2 x 240 ml) and drying at about 400C overnight to afford the title compound as a pale yellow solid (74.24 g, 71% yield).
IH NMR (400MHz, DMSO-d6) δ: 7.72-7.65 (m, 2H), 7.63-7.56 (m, IH), 7.49-7.42 (m, IH),
7.03 (s, IH).
13C NMR (400MHz, DMSO-d6) δ: 162.0 (d, J = 245 Hz), 149.3 (d, J = 3 Hz), 135.6 (d, J= 8
Hz), 131.1 (d, J = 9 Hz), 123.3 (d, J = 3 Hz), 118.8 (d, J = 21 Hz), 115.8, 113.8 (d, J = 24 Hz),
1H NMR (400 MHz, DMSO-d6, 300 K): 7.72–7.65 (m, 2H), 7.63–7.56 (m, 1H), 7.49–7.42 (m, 1H), 7.03 (s, 1H). 13C NMR (100 MHz, DMSO-d6, 300 K): 162.0 (d, J = 245 Hz), 149.3 (d, J = 3 Hz), 135.6 (d, J = 8 Hz), 131.1 (d, J = 9 Hz), 123.3 (d, J = 3 Hz), 118.8 (d, J = 21 Hz), 115.8 (s), 113.8 (d, J = 24 Hz), 99.3 (s). GC-HRMS Calcd for [M] C9H5NFCl: 181.0095; found [M]+: 181.0090.