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884504-63-6

4-(3-BROMOPHENYL)-4-OXOBUTYRONITRILE synthesis

3synthesis methods
-

Yield:884504-63-6 58%

Reaction Conditions:

with sodium cyanide in N,N-dimethyl-formamide at 35; for 3 h;

Steps:

14.a

Step a) 4-(3-Bromophenyl)-4-oxo-butyronitrile A mixture of powder sodium cyanide (1.23 g, 25 mmol) in DMF was treated 5 slowly with a solution of 3-bromo-benzaldehyde in DMF, stirred at 35° C. for 3 hours, cooled to room temperature, poured into a cold 0.5 N HCl solution and extracted with ethyl ether. The extracts were combined, washed with saturated aqueous sodium bicarbonate, brine, dried over MgSO4 and concentrated in vacuo. The resultant residue was triturated in ethyl ether and filtered. The filtercake was dried to give 4-(3-bromophenyl)-4-oxo-butyronitrile as a yellow solid (4 g, 58% yield). m/e (M)+ 237. 1H NMR (400 MHZ, DMSO-d6) δ ppm, 2.7 (t, J=6.7 Hz, 2 H), 3.5 (t, J=6.7 Hz, 2 H), 7.5 (t, J=7.8 Hz, 1 H), 7.9 (ddd, J=7.9, 2.1, 0.9 Hz, 1 H), 8.0 (ddd, J=7.8, 1.7, 0.9 Hz, 1 H), 8.1 (t, J=1.7 Hz, 1 H).

References:

US2007/72925,2007,A1 Location in patent:Page/Page column 22; 23