ChemicalBook CAS DataBase List 2-CHLOROBENZOYLACETONITRILE

2-CHLOROBENZOYLACETONITRILE synthesis

10synthesis methods

Product Name:2-CHLOROBENZOYLACETONITRILE
CAS Number:40018-25-5
Molecular formula:C9H6ClNO
Molecular Weight:179.6

609-65-4 Synthesis

609-65-4
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$19.00/25mL

372-09-8
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$20.00/25g

40018-25-5
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$9.00/1g

Yield:40018-25-5 77%

Reaction Conditions:

Stage #1:cyanoacetic acid with n-butyllithium in tetrahydrofuran;hexane at -78 - 0;
Stage #2:o-chlorobenzoyl chloride in tetrahydrofuran;hexane at -70 - 20;

Steps:

1 1. Synthesis of (2-Chlorobenzoyl)acetonitrile (2)
A solution of cyanoacetic acid (5 g, 0.059 mol) and 2,2'-bipyridine (2 mg, as indicator) in 300 mL of dry THF, was cooled to -78° C. with stirring, under nitrogen atmosphere. To this mixture, n-BuLi, 1.6 M in hexane (73 mL, 0.116 mol) was dropwise added, allowing the reaction temperature to slowly rise to 0° C. [0022] When the red color persisted at 0° C., the slurry was recooled to -70° C. and then, (2-chloro)benzoyl chloride (5.14 g, 0.029 mol) in 50 mL of dry THF was dropwise added. The slurry was stirred at -70° C. for 1 hour, and then allowed to rise to room temperature. [0023] Then, hydrochloric acid 1N (100 mL) was added to the mixture, which was extracted with EtOAc (3×75 mL), and the combined organic extracts were washed with saturated sodium hydrogen carbonate solution (2×75 mL) and brine (2×75 mL). The organic layer was then dried over sodium sulfate, filtered and evaporated under reduced pressure to give a residue which was purified by silica gel chromatography. Elution with hex/EtOAc (7:3) gave the title compound as a yellow solid (4.06 g, 77%). M.p.56-58° C. (EtOH) [0024] IR (KBr): 2961, 2210, 1709, 1590, 1433, 1320, 1251, 1053 cm-1. 1H NMR (CDCl3, 300 MHz) δ: 7.62 (d, 1H, J=7.8 Hz), 7.50-7.39 (m, 3H), 4.14 (s,2H) ppm. [0025] Analysis, calculated for C9H6ClNO (179.61 g/mol) % C % H % N Calculated 60.19 3.37 7.80 Found 60.63 3.53 7.63

References:

Bazan, Nicholas G;Gomez, Julio Alvarez Builla US2003/229078, 2003, A1 Location in patent:Page 3

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