76574-42-0|2-(3-Bromo-2-methylphenyl)acetonitrile| Ambeed

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Quality Control of [ 76574-42-0 ] Purity: 95% SDS Specification

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Product Details of [ 76574-42-0 ]

CAS No. :	76574-42-0
Formula :	C₉H₈BrN
M.W :	210.07
SMILES Code :	N#CCC1=CC=CC(Br)=C1C
MDL No. :	MFCD18392229
InChI Key :	VBNCKBSHNGLORC-UHFFFAOYSA-N
Pubchem ID :	20480065

Safety of [ 76574-42-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Application In Synthesis of [ 76574-42-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 76574-42-0 ]

[ 76574-42-0 ] Synthesis Path-Downstream 1~24

1
[ 576-23-8 ]
[ 151-50-8 ]
[ 76574-41-9 ]
[ 76574-42-0 ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 382 - 389.

2
[ 83647-43-2 ]
[ 76574-42-0 ]

References: [1]Patent: WO2015/105779,2015,A1 .
[2]Patent: WO2017/158151,2017,A1 .
[3]ACS Medicinal Chemistry Letters,2019,vol. 10,p. 74 - 79.

3
[ 773837-37-9 ]
[ 112299-62-4 ]
[ 76574-42-0 ]

Yield	Reaction Conditions	Operation in experiment
28.2%	In N,N-dimethyl-formamide; at 100℃; for 12h;	To a solution of bromo-3-bromomethyl-2-methyl-benzene (0.2 g, 7.6 mmol) in DMF (15 mL) is added sodium cyanide (0.55 g, 11.4 mmol) at room temperature. The reaction mixture is heated at 100 C for 12 hours and quenched with potassium permanganate solution, filtered, and the filtrate is diluted with water and extracted with EtOAc (2x20 mL). The organic extracts are dried over Na2SO4, filtered, and evaporated. The crude material is purified over silica gel column chromatography (combiflash),eluting with EtOAc 10-25% in hexanes to give the title compound (0.8 g, 28.2%). LCMS m/z 211 [M+Hjt
28.2%	In N,N-dimethyl-formamide; at 20 - 100℃; for 12h;	To a solution of bromo-3-bromomethyl-2-methyl-benzene (0.2 g, 7 6 mmol) in DMF (15 mL) is added sodium cyanide (0.55 g, 11.4 mmol) at room temperature. The reaction mixture is heated at 100 C. for 12 hours and quenched with potassium permanganate solution, filtered, and the filtrate is diluted with water and extracted with EtOAc (2*20 mL). The organic extracts are dried over Na2SO4, filtered, and evaporated. The crude material is purified over silica gel column chromatography (combiflash), eluting with EtOAc 10-25% in hexanes to give the title compound (0.8 g, 28.2%). LC-MS m/z 211 [M+H]+.

References: [1]Patent: WO2015/105779,2015,A1 .Location in patent: Page/Page column 27.
[2]Patent: US2016/333005,2016,A1 .Location in patent: Paragraph 0090-0091.

4
[ 76574-42-0 ]
[ 74-88-4 ]
2-(3-bromo-2-methyl-phenyl)-2-methyl-propionitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75.9%		To a solution of NaH (0.22 g, 5.6 mmol, 60% in paraffin oil) in THF at 0 C is added a solution of <strong>[76574-42-0](3-bromo-2-methyl-phenyl)-acetonitrile</strong> (0.6 g, 2.8 mmol) in THF (4 mL). The reaction mixture is stirred at room temperature for 30 minutes and then methyliodide (0.43 mL, 7 mmol) is added. The reaction mixture is stirred at room temperature for 12 hours, quenched with saturated aqueous NH4C1 solution, and extracted in EtOAc (2x25 mL). The organic layer is washed with brine (10 mL), dried over Na2SO4, filtered, and evaporated. The crude of another lot (1 g) is combined with this lot and purified over silica gel column chromatography (combiflash), eluting with 10-30% EtOAc inhexanes to give the title compound (1.2 g, 75.9%). LC-MS m/z 239 [M+Hj.
75.9%		To a solution of NaH (0.22 g, 5.6 mmol, 60% in paraffin oil) in THF at 0 C. is added a solution of <strong>[76574-42-0](3-bromo-2-methyl-phenyl)-acetonitrile</strong> (0.6 g, 2.8 mmol) in THF (4 mL). The reaction mixture is stirred at room temperature for 30 minutes and then methyl iodide (0.43 mL, 7 mmol) is added. The reaction mixture is stirred at room temperature for 12 hours, quenched with saturated aqueous NH4Cl solution, and extracted in EtOAc (2*25 mL). The organic layer is washed with brine (10 mL), dried over Na2SO4, filtered, and evaporated. The crude of another lot (1 g) is combined with this lot and purified over silica gel column chromatography (combiflash), eluting with 10-30% EtOAc in hexanes to give the title compound (1.2 g, 75.9%). LC-MS m/z 239 [M+H]+.

References: [1]Patent: WO2015/105779,2015,A1 .Location in patent: Page/Page column 33.
[2]Patent: US2016/333005,2016,A1 .Location in patent: Paragraph 0108-0109.

5
potassium cyanide [ No CAS ]
[ 1148024-99-0 ]
[ 76574-42-0 ]

Yield	Reaction Conditions	Operation in experiment
3.8 g	In N,N-dimethyl-formamide; at 20℃; for 16h;	To a stirred solution of (3-bromo-2-methyl-phenyl)methyl methanesulfonate (6 g, 21 .5 mmol) in DMF (30 mL) was added KCN (1.68 g, 25.80 mmol) and the reaction mixture was stirred at room temperature for 16h. The reaction mixture was quenched with saturated sodium bicarbonate solution and stirring continued for 30 min. The aqueous phase was extracted with DCM (100 mL x 2). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated. The residue was purified by flash column chromatography (10% EtOAc in hexane) to get the title compound (3.8 g, 83% yield over two steps) as a viscous oil

References: [1]Patent: WO2017/158151,2017,A1 .Location in patent: Page/Page column 149.
[2]ACS Medicinal Chemistry Letters,2019,vol. 10,p. 74 - 79.

6
[ 83647-40-9 ]
[ 76574-42-0 ]

References: [1]Patent: WO2017/158151,2017,A1 .

7
[ 76574-42-0 ]
1-(2-methyl-3-vinyl-phenyl)cyclopentanecarbonitrile [ No CAS ]

References: [1]Patent: WO2017/158151,2017,A1 .

8
[ 76574-42-0 ]
1-(3-ethyl-2-methyl-phenyl)cyclopentanecarbonitrile [ No CAS ]

References: [1]Patent: WO2017/158151,2017,A1 .

9
[ 110-52-1 ]
[ 76574-42-0 ]
1-(3-bromo-2-methyl-phenyl)cyclopentanecarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium hydride; In diethyl ether; dimethyl sulfoxide; at 20℃; for 16h;	To an ice cooled suspension of NaH (1 g, 41.90 mmol) in DMSO (25 mL) was added a solution of <strong>[76574-42-0]2-(3-bromo-2-methyl-phenyl)acetonitrile</strong> (4 g, 19 mmol) and 1 ,4 dibromobutane (2.73 mL, 22.85 mmol) in DMSO-diethyl ether (50 mL, 1 :1 ) and the reaction mixture was stirred for 16h at room temperature. The reaction mixture was quenched with saturated ammonium chloride and extracted with EtOAc (50 mL x 2). The combined organic layers were washed with brine, dried over anhydrous sodium sulphate, filtered and concentrated. The residue was purified by flash column (5% EtOAc in hexane) to get the title compound (3.8 g, 75%) as a colorless oil.

References: [1]Patent: WO2017/158151,2017,A1 .Location in patent: Page/Page column 149; 150.

10
[ 76006-33-2 ]
[ 76574-42-0 ]