123843-66-3|2,6-Difluoro-4-methoxybenzonitrile| Ambeed

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Quality Control of [ 123843-66-3 ] Purity: 97% SDS Specification

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Product Details of [ 123843-66-3 ]

CAS No. :	123843-66-3
Formula :	C₈H₅F₂NO
M.W :	169.13
SMILES Code :	COC1=CC(F)=C(C#N)C(F)=C1
MDL No. :	MFCD03094498
InChI Key :	CMGFDVIQHBAJHT-UHFFFAOYSA-N
Pubchem ID :	2778772

Safety of [ 123843-66-3 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302+H312-H315-H319-H331-H335
Precautionary Statements:	P261-P280-P305+P351+P338-P311
Class:	6.1
UN#:	3439
Packing Group:	Ⅲ

Application In Synthesis of [ 123843-66-3 ]

* 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 [ 123843-66-3 ]

[ 123843-66-3 ] Synthesis Path-Downstream 1~35

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[ 123843-66-3 ]
[ 123843-57-2 ]

References: [1]Molecular Crystals and Liquid Crystals (1969-1991),1989,vol. 172,p. 165 - 190.

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Yield	Reaction Conditions	Operation in experiment
91%	With thionyl chloride; In N,N-dimethyl-formamide; at 0 - 20℃;	To a solution of 2, 6-difluoro-4-methoxybenzamide (55 g, 294.1 mmol) in DMF (300 mL) was added a mixture of SOCl 2 (350 g) in DMF at 0. The resulting mixture was stirred at room temperature overnight. The reaction mixture was poured into ice-water (1 L) and extracted with EtOAc (1 L x3) . The combined organic layer was dried over anhydrous Na 2SO 4 and filtered. The filtrate was concentrated. The residue was purified by silica gel chromatography (PE/EtOAc = 5/1) to give the product (45 g, 91%yield) as a white solid. MS (ESI) m/z: 170.1 (M+H) +.

References: [1]Molecular Crystals and Liquid Crystals (1969-1991),1989,vol. 172,p. 165 - 190.
[2]Patent: WO2020/57511,2020,A1 .Location in patent: Page/Page column 176; 178.
[3]Heterocycles,2006,vol. 67,p. 489 - 494.

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[ 601517-02-6 ]

Yield	Reaction Conditions	Operation in experiment
91%	With dihexyl phthalate; ammonia; In dimethyl sulfoxide; at 80℃;Sealed tube;	To a solution of 2, 6-difluoro-4-methoxybenzonitrile (45 g, 266.3 mmol) in DMSO (400 mL) was added DHP (1.0 mL, 12.40 mmol) . Then ammonia was bubbled through the reaction mixture about 10 min and then the reaction mixture was sealed. After stirred at 80 overnight, the reaction mixture was diluted with water (300 mL) and extracted with EtOAc (300 mL x3) . The combined organic layer was washed with water (300 mL x3) and brine (300 mL) , dried over anhydrous Na 2SO 4, filtered and concentrated to give a residue. The residue was purified by silica gel chromatography (PE/EtOAc = 1/3) to give the product (40 g, 91%yield) as a white solid. MS (ESI) m/z: 167.1 (M+H) +.
86%	With ammonium hydroxide; In isopropyl alcohol; at 80℃; for 16.0h;Sealed tube; Inert atmosphere;	Ammonium hydroxide (5.2 mL, 41.4 mmol) was added to a microwave vial containing 2,6-difluoro-4-methoxybenzonitrile (1 g, 5.9 mmol) in isopropanol (1 mL). The resulting solution was sealed and stirred at 80 C. for 16 hours. The reaction mixture was concentrated and ethyl acetate (75 mL) was added. The organic layer were isolated and washed with saturated brine (10 mL) then evaporated to afford the title compound (0.8 g, 86%) which was used without further purification. 1H NMR (500 MHz, DMSO, 27 C.) δ 3.72 (3H, s), 6.11 (1H, dd), 6.15 (1H, dd), 6.36 (2H, s); m/z: ES- [M-H]- 165.
67.8%	With ammonia; In dimethyl sulfoxide; at 90℃; for 16.0h;Sealed tube;	<strong>[123843-66-3]2,6-Difluoro-4-methoxybenzonitrile</strong> (12.0g, 71.0mmol) was added to a sealed tube containing DMSO (50mL), ammonia gas was introduced into the system for three minutes, and then reacted at 90C for 16 hours. The temperature of the system was lowered to 25C, EA (150mL) and water (100mL) were added for extraction and liquid separation, the organic phase was concentrated and purified by silica gel column chromatography (PE:EA=3:1) to obtain the product (8.0g, yield 67.8%) .

	With ammonia; In dimethyl sulfoxide;	Step 1: 2-Amino-6-fluoro-4-methoxybenzonitrile Ammonia gas was bubbled through a solution of 2,6-difluoro-4-methoxybenzonitrile (1.0 g, 5.91 mmol) in dimethylsulfoxide (11.83 mL) for 10 minutes. The reaction was then sealed and stirred at 90 C. for 24 hours. The reaction mixture was cooled to ambient temperature and concentrated in vacuo to afford a tan residue. The residue was triturated with water, collected be vacuum filtration, and dried in vacuo to afford the title intermediate (0.9 g, 5.42 mmol) as a white solid. LC/MS (ESI+) m/z=167 (M+H).
0.9 g	With ammonia; In dimethyl sulfoxide; at 90℃; for 24.0h;	Ammonia gas was bubbled through a solution of 2,6-difluoro-4-methoxybenzonitrile (1.0 g, 5.91 mmol) in dimethylsulfoxide (11.83 mL) for 10 minutes. The reaction was then sealed and stirred at 90 C. for 24 hours. The reaction mixture was cooled to ambient temperature and concentrated in vacuo to afford a tan residue. The residue was triturated with water, collected be vacuum filtration, and dried in vacuo to afford the title intermediate (0.9 g, 5.42 mmol) as a white solid. LC/MS (ESI+) m/z=167 (M+H
	With ammonia; In dimethyl sulfoxide;	Step 1: 2-Amino-6-fluoro-4-methoxybenzonitrile Ammonia gas was bubbled through a solution of 2,6-difluoro-4-methoxybenzonitrile (1.0 g, 5.91 mmol) in dimethylsulfoxide (11.83 mL) for 10 minutes. The reaction was then sealed and stirred at 90 C. for 24 hours. The reaction mixture was cooled to ambient temperature and concentrated in vacuo to afford a tan residue. The residue was triturated with water, collected be vacuum filtration, and dried in vacuo to afford the title intermediate (0.9 g, 5.42 mmol) as a white solid. LC/MS (ESI+) m/z=167 (M+H).
0.9 g	With ammonia; In dimethyl sulfoxide; at 90℃; for 24.0h;	Ammonia gas was bubbled through a solution of 2,6-difluoro-4- methoxybenzonitrile (1.0 g, 5.91 mmol) in dimethylsulfoxide (11.83 mL) for 10 minutes. The reaction was then sealed and stirred at 90 C for 24 hours. The reaction mixture was cooled to RT and concentrated in vacuo to afford a tan residue. The residue was triturated with water, collected be vacuum filtration, and dried in vacuo to afford the title intermediate (0.9 g, 5.42 mmol) as a white solid. LC/MS (ESI) m/z = 167 (M+H)+
0.9 g	With ammonia; In dimethyl sulfoxide; at 90℃; for 24.17h;Sealed tube;	Ammonia gas was bubbled through a solution of 2,6-difluoro-4-methoxybenzonitrile (1.0 g, 5.91 mmol) in dimethylsulfoxide (11.83 mL) for 10 minutes. The reaction was then sealed and stirred at 90 C. for 24 hours. The reaction mixture was cooled to ambient temperature and concentrated in vacuo to afford a tan residue. The residue was triturated with water, collected be vacuum filtration, and dried in vacuo to afford the title intermediate (0.9 g, 5.42 mmol) as a white solid. LC/MS (ESI+) m/z=167 (M+H).
0.9 g	With ammonia; In dimethyl sulfoxide; at 90℃; for 24.0h;Sealed tube;	Ammonia gas was bubbled through a solution of 2,6-difluoro-4-methoxybenzonitrile (1.0 g, 5.91 mmol) in DMSO (11.83 mL) for 10 minutes. The reaction was then sealed and stirred at 90 C for 24 h. The reaction mixture was cooled to RT and concentrated in vacuo to afford a tan residue. The residue was triturated with water, collected be vacuum filtration, and dried in vacuo to afford the title intermediate (0.9 g, 5.42 mmol) as a white solid. LC/MS (ESI+) m/z = 167 (M+H) +.

References: [1]Patent: WO2020/57511,2020,A1 .Location in patent: Page/Page column 176; 178.
[2]Heterocycles,2006,vol. 67,p. 489 - 494.
[3]Journal of Medicinal Chemistry,2018,vol. 61,p. 8797 - 8810.
[4]Patent: US2018/312490,2018,A1 .Location in patent: Paragraph 0241; 0410.
[5]Patent: CN111635373,2020,A .Location in patent: Paragraph 0220-0223.
[6]Patent: US2014/107109,2014,A1 .Location in patent: Page/Page column.
[7]Patent: US2014/213581,2014,A1 .Location in patent: Paragraph 0634.
[8]Patent: US2014/249104,2014,A1 .Location in patent: Page/Page column.
[9]Patent: WO2014/138484,2014,A1 .Location in patent: Page/Page column 146.
[10]Patent: US2015/38497,2015,A1 .Location in patent: Paragraph 0798.
[11]Patent: WO2016/22724,2016,A1 .Location in patent: Page/Page column 319.
[12]Patent: WO2019/214634,2019,A1 .Location in patent: Page/Page column 52; 53.

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References: [1]Heterocycles,2006,vol. 67,p. 489 - 494.
[2]Molecular Crystals and Liquid Crystals (1969-1991),1989,vol. 172,p. 165 - 190.
[3]Patent: WO2020/57511,2020,A1 .

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[ 123843-66-3 ]
[ 601516-55-6 ]