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ChemicalBook CAS DataBase List 3,5-Dichlorobenzonitrile
6575-00-4

3,5-Dichlorobenzonitrile synthesis

4synthesis methods
1-Bromo-3,5-dichlorobenzene

19752-55-7

3,5-Dichlorobenzonitrile

6575-00-4

General procedure for the synthesis of 3,5-dichlorobenzonitrile from 3,5-dichloro-1-bromobenzene: iPrMgCl (2M in THF, 4.1 mL) and THF (5 mL) were added to a flask containing dry LiCl (0.35 g, 8.24 mmol) at 15 °C. After stirring for 15 min, a solution of 3,5-dichloro-1-bromobenzene (1.46 g, 8.03 mmol) in THF (1 mL) was slowly added to the reaction mixture and stirring was continued for 15 min. Subsequently, the reaction mixture was cooled to 0 °C, DMF (1.3 mL, 12 mmol) was added and stirred at this temperature for 2 hours. Upon completion of the reaction, aqueous NH3 (7 mL, 28-30%) and I2 (4.06 g, 16 mmol) were sequentially added to the mixture. After stirring for 2 h at room temperature, the reaction mixture was poured into saturated aqueous Na2SO3 solution and extracted with CHCl3 (3 x 30 mL). The organic layers were combined, dried with Na2SO4 and filtered. After removing the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 9:1, v/v) to afford pure 3,5-dichlorobenzonitrile (0.73 g) in 71% yield. Most of the nitrile compounds involved in this study were commercially available and were identified by comparison with real samples.

19752-55-7 Synthesis
1-Bromo-3,5-dichlorobenzene

19752-55-7
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$8.00/10g

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Yield:6575-00-4 72%

Reaction Conditions:

Stage #1:1-bromo-3,5-dichlorobenzene with isopropylmagnesium chloride;lithium chloride in tetrahydrofuran at -15; for 0.25 h;
Stage #2: with N,N-dimethyl-formamide in tetrahydrofuran at 0; for 2 h;
Stage #3: with ammonia;iodine in tetrahydrofuran;water at 20; for 2 h;

Steps:

3.28 Typical experimental procedure for conversion of aromaticbromides into aromatic nitriles with iPrMgCl, DMF, I2,and aq NH3
General procedure: To a flask containing dried LiCl (0.35 g, 8.24 mmol) was added iPrMgCl (2 M in THF, 4.1 mL) and THF (5 mL) at 15° C. After beingstirred for 15 min, 3-bromo-1-benzonitrile (1.46 g, 8.03 mmol) inTHF (1 mL) was added to the reaction mixture and the obtainedmixture was stirred for 15 min. Then, DMF (1.3 mL, 12 mmol) wasadded at 0° C and the mixture was stirred for 2 h. Then, aq NH3 (7 mL, 28-30%) and I2 (4.06 g, 16 mmol) were added to the reaction mixture. After being stirred for 2 h at room temperature, the reactionmixture was poured into satd aq Na2SO3 solution and was extracted with CHCl3 (3∗30 mL). The organic layer was dried over Na2SO4 and filtered. After removal of the solvent, the residue waspurified by short column chromatography on silica gel (eluent:hexane/ethyl acetate=9:1, v/v) to provide pure 1,3-dicyanobenzene (0.73 g) in 71% yield. Most nitriles mentioned in this work are commercially availableand were identified by comparison with the authentic samples.

References:

Ishii, Genki;Harigae, Ryo;Moriyama, Katsuhiko;Togo, Hideo [Tetrahedron,2013,vol. 69,# 5,p. 1462 - 1469]

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