[ CAS No. 63878-68-2 ] {[proInfo.proName]}

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Quality Control of [ 63878-68-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 63878-68-2 ]

Product Details of [ 63878-68-2 ]

CAS No. :	63878-68-2	MDL No. :	MFCD28134444
Formula :	C₇H₅F₂NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	173.12	Pubchem ID :	-
Synonyms :

Safety of [ 63878-68-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 63878-68-2 ]

* 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.

Upstream synthesis route of [ 63878-68-2 ]
Downstream synthetic route of [ 63878-68-2 ]

[ 63878-68-2 ] Synthesis Path-Upstream 1~3

1
[ 63878-73-9 ]
[ 63878-68-2 ]

Yield	Reaction Conditions	Operation in experiment
4.5 g	With diethylamino-sulfur trifluoride In dichloromethane at -78℃; Inert atmosphere	To a solution of Compound 2 (6.2 g, 36.3 mmol) in anhydrous DCM (80 mL) was added DAST (11.7 g, 34.3 mmol) drop-wise at -78 °C under N₂. The reaction mixture was stirred at rt for 2 h, and poured into a beaker containing 30 g of ice, decomposing any unreacted DAST. Mixture was extracted twice with 45 mL portions of DCM. The combined organic layer was washed with 50 mL of water, and dried over anhydrous magnesium sulfate. Evaporation to dryness under reduced pressure gives crude product which was purified by silica gel chromatography (eluted with PE: EA=froml00: 1 to 50: 1) to afford Compound 3. (4.5 g, yield: 71percent)
3.9 g	With diethylamino-sulfur trifluoride In dichloromethane at -30 - 10℃;	Compound 127 (2-fluoro-5-nitro-phenyl)methanol (4.3 g, 25.1 mmol) was dissolved in dichloro- methane (50 mL). Diethylaminosulfur trifluoride (4.5 g, 27.9 mmol) was added drop wise to the mixture at -30°C. The mixture was stirred at 10° C for 4 hours. Methanol (10 mL) was added to the mixture and the mixture was further stirred at 10°C for 30 minutes. The mixture was washed with brine (30mL) and the aqueous layer was extracted with CH₂C1₂ (2 x 30 mL). The combined organic layers were dried over Na₂S0₄ and concentrated in vacuo, resulting in l-fluoro-2-(fluoromethyl)-4-nitro- benzene (3.9 g). A mixture of l-fluoro-2-(fluoromethyl)-4-nitro-benzene (3.1 g, 17.9 mmol), iron (4.0 g, 71.6 mmol) and methanol (30 mL) was stirred at 65° for 8 hours. The mixture was filtrated and the filtrate was concentrated in vacuo, resulting in 4-fluoro-3-(fluoromethyl)aniline (1.5 g). 3-(chlorosulfonyl)benzoyl chloride (300 mg, 1.2 mmol) and triethylamine (150 mg, 1.5 mmol) were dissolved in dichloromethane (20 mL). 4-fluoro-3-(fluoromethyl)aniline (175 mg, 1.22 mmol) was added to the mixture at 0° C. The mixture was stirred at 10°C for 30 minutes. The mixture was used to the next step without further purification.Triethylamine (152 mg, 1.5 mmol) and 3-methyl-3-oxetanamine (131 mg. 1.5 mmol) were added to the above obtained reaction mixture at 0° C. The mixture was stirred at 20° C for 1 hour. The solvent was removed in vacuo and the obtained residue was purified by reversed phase high performance liquid chromatography (Column: Gemini 25020mm5um.. A: H₂O+0.1percentTFA B: MeCN. 27percent to 57percent B in A). The product fractions were collected and the organic solvent was removed in vacuo. The fraction was neutralized by saturated NaHC03. The mixture was extracted with dichloromethane (3 x 20 mL) and the combined organic layer was dried over Na₂S0₄ and concentrated in vacuo, resulting in compound 127 (91.1 mg). Method A; Rt: 4.95 min. m/z : 397.3 (M+H)⁺ Exact mass: 396.1. 1H NMR (400 MHz, DMSO-d₆) δ ppm 1.41 (s, 3 H) 4.14 (d, J=6.3 Hz, 2 H) 4.56 (d, J=6.3 Hz, 2 H) 5.52 (d, J=48 Hz, 2 H) 7.31 (t, J=9.4 Hz, 1 H) 7.72 - 7.89 (m, 2 H) 7.92-7.97 (m, 1 H) 8.03 (d, J=8.0 Hz, 1 H) 8.23 (d, J=7.8 Hz, 1 H) 8.39 (s, 1 H) 8.55 (s, 1 H) 10.67 (s, 1 H).
3.9 g	With diethylamino-sulfur trifluoride In dichloromethane at -30 - 10℃; for 4 h;	Compound 127 (2-fluoro-5-nitro-phenyl)methanol (4.3 g, 25.1 mmol) was dissolved in dichloro- methane (50 mL). Diethylaminosulfur trifluoride (4.5 g, 27.9 mmol) was added drop wise to the mixture at -30°C. The mixture was stirred at 10° C for 4 hours. Methanol (10 mL) was added to the mixture and the mixture was further stirred at 10°C for 30 minutes. The mixture was washed with brine (30mL) and the aqueous layer was extracted with CH₂C1₂ (2 x 30 mL). The combined organic layers were dried over Na₂S0₄ and concentrated in vacuo, resulting in l-fluoro-2-(fluoromethyl)-4-nitro- benzene (3.9 g). A mixture of l-fluoro-2-(fluoromethyl)-4-nitro-benzene (3.1 g, 17.9 mmol), iron (4.0 g, 71.6 mmol) and methanol (30 mL) was stirred at 65° for 8 hours. The mixture was filtrated and the filtrate was concentrated in vacuo, resulting in 4-fluoro-3-(fluoromethyl)aniline (1.5 g). 3-(chlorosulfonyl)benzoyl chloride (300 mg, 1.2 mmol) and triethylamine (150 mg, 1.5 mmol) were dissolved in dichloromethane (20 mL). 4-fluoro-3-(fluoromethyl)aniline (175 mg, 1.22 mmol) was added to the mixture at 0° C. The mixture was stirred at 10°C for 30 minutes. The mixture was used to the next step without further purification.Triethylamine (152 mg, 1.5 mmol) and 3-methyl-3-oxetanamine (131 mg. 1.5 mmol) were added to the above obtained reaction mixture at 0° C. The mixture was stirred at 20° C for 1 hour. The solvent was removed in vacuo and the obtained residue was purified by reversed phase high performance liquid chromatography (Column: Gemini 25020mm5um.. A: H₂O+0.1percentTFA B: MeCN. 27percent to 57percent B in A). The product fractions were collected and the organic solvent was removed in vacuo. The fraction was neutralized by saturated NaHC03. The mixture was extracted with dichloromethane (3 x 20 mL) and the combined organic layer was dried over Na₂S0₄ and concentrated in vacuo, resulting in compound 127 (91.1 mg). Method A; Rt: 4.95 min. m/z : 397.3 (M+H)⁺ Exact mass: 396.1. 1H NMR (400 MHz, DMSO-d₆) δ ppm 1.41 (s, 3 H) 4.14 (d, J=6.3 Hz, 2 H) 4.56 (d, J=6.3 Hz, 2 H) 5.52 (d, J=48 Hz, 2 H) 7.31 (t, J=9.4 Hz, 1 H) 7.72 - 7.89 (m, 2 H) 7.92-7.97 (m, 1 H) 8.03 (d, J=8.0 Hz, 1 H) 8.23 (d, J=7.8 Hz, 1 H) 8.39 (s, 1 H) 8.55 (s, 1 H) 10.67 (s, 1 H).

Reference： [1] Australian Journal of Chemistry, 1977, vol. 30, p. 1611 - 1615
[2] Patent: WO2013/96744, 2013, A1, . Location in patent: Page/Page column 226
[3] Patent: WO2014/33170, 2014, A1, . Location in patent: Page/Page column 69; 70
[4] Patent: WO2014/33176, 2014, A1, . Location in patent: Page/Page column 69-70

2
[ 455-88-9 ]
[ 63878-68-2 ]

Reference： [1] Journal of Fluorine Chemistry, 1996, vol. 77, # 1, p. 65 - 70

3
[ 27996-87-8 ]
[ 63878-68-2 ]

Reference： [1] Patent: WO2013/96744, 2013, A1,

[ 63878-68-2 ] Synthesis Path-Downstream 1~1

1
[ 63878-73-9 ]
[ 63878-68-2 ]

Yield	Reaction Conditions	Operation in experiment
4.5 g	With diethylamino-sulfur trifluoride; In dichloromethane; at -78℃;Inert atmosphere;	To a solution of Compound 2 (6.2 g, 36.3 mmol) in anhydrous DCM (80 mL) was added DAST (11.7 g, 34.3 mmol) drop-wise at -78 C under N2. The reaction mixture was stirred at rt for 2 h, and poured into a beaker containing 30 g of ice, decomposing any unreacted DAST. Mixture was extracted twice with 45 mL portions of DCM. The combined organic layer was washed with 50 mL of water, and dried over anhydrous magnesium sulfate. Evaporation to dryness under reduced pressure gives crude product which was purified by silica gel chromatography (eluted with PE: EA=froml00: 1 to 50: 1) to afford Compound 3. (4.5 g, yield: 71%)
3.9 g	With diethylamino-sulfur trifluoride; In dichloromethane; at -30 - 10℃;	Compound 127 (2-fluoro-5-nitro-phenyl)methanol (4.3 g, 25.1 mmol) was dissolved in dichloro- methane (50 mL). Diethylaminosulfur trifluoride (4.5 g, 27.9 mmol) was added drop wise to the mixture at -30C. The mixture was stirred at 10 C for 4 hours. Methanol (10 mL) was added to the mixture and the mixture was further stirred at 10C for 30 minutes. The mixture was washed with brine (30mL) and the aqueous layer was extracted with CH2C12 (2 x 30 mL). The combined organic layers were dried over Na2S04 and concentrated in vacuo, resulting in l-fluoro-2-(fluoromethyl)-4-nitro- benzene (3.9 g). A mixture of l-fluoro-2-(fluoromethyl)-4-nitro-benzene (3.1 g, 17.9 mmol), iron (4.0 g, 71.6 mmol) and methanol (30 mL) was stirred at 65 for 8 hours. The mixture was filtrated and the filtrate was concentrated in vacuo, resulting in 4-fluoro-3-(fluoromethyl)aniline (1.5 g). 3-(chlorosulfonyl)benzoyl chloride (300 mg, 1.2 mmol) and triethylamine (150 mg, 1.5 mmol) were dissolved in dichloromethane (20 mL). 4-fluoro-3-(fluoromethyl)aniline (175 mg, 1.22 mmol) was added to the mixture at 0 C. The mixture was stirred at 10C for 30 minutes. The mixture was used to the next step without further purification.Triethylamine (152 mg, 1.5 mmol) and 3-methyl-3-oxetanamine (131 mg. 1.5 mmol) were added to the above obtained reaction mixture at 0 C. The mixture was stirred at 20 C for 1 hour. The solvent was removed in vacuo and the obtained residue was purified by reversed phase high performance liquid chromatography (Column: Gemini 25020mm5um.. A: H2O+0.1%TFA B: MeCN. 27% to 57% B in A). The product fractions were collected and the organic solvent was removed in vacuo. The fraction was neutralized by saturated NaHC03. The mixture was extracted with dichloromethane (3 x 20 mL) and the combined organic layer was dried over Na2S04 and concentrated in vacuo, resulting in compound 127 (91.1 mg). Method A; Rt: 4.95 min. m/z : 397.3 (M+H)+ Exact mass: 396.1. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.41 (s, 3 H) 4.14 (d, J=6.3 Hz, 2 H) 4.56 (d, J=6.3 Hz, 2 H) 5.52 (d, J=48 Hz, 2 H) 7.31 (t, J=9.4 Hz, 1 H) 7.72 - 7.89 (m, 2 H) 7.92-7.97 (m, 1 H) 8.03 (d, J=8.0 Hz, 1 H) 8.23 (d, J=7.8 Hz, 1 H) 8.39 (s, 1 H) 8.55 (s, 1 H) 10.67 (s, 1 H).
3.9 g	With diethylamino-sulfur trifluoride; In dichloromethane; at -30 - 10℃; for 4.0h;	Compound 127 (2-fluoro-5-nitro-phenyl)methanol (4.3 g, 25.1 mmol) was dissolved in dichloro- methane (50 mL). Diethylaminosulfur trifluoride (4.5 g, 27.9 mmol) was added drop wise to the mixture at -30C. The mixture was stirred at 10 C for 4 hours. Methanol (10 mL) was added to the mixture and the mixture was further stirred at 10C for 30 minutes. The mixture was washed with brine (30mL) and the aqueous layer was extracted with CH2C12 (2 x 30 mL). The combined organic layers were dried over Na2S04 and concentrated in vacuo, resulting in l-fluoro-2-(fluoromethyl)-4-nitro- benzene (3.9 g). A mixture of l-fluoro-2-(fluoromethyl)-4-nitro-benzene (3.1 g, 17.9 mmol), iron (4.0 g, 71.6 mmol) and methanol (30 mL) was stirred at 65 for 8 hours. The mixture was filtrated and the filtrate was concentrated in vacuo, resulting in 4-fluoro-3-(fluoromethyl)aniline (1.5 g). 3-(chlorosulfonyl)benzoyl chloride (300 mg, 1.2 mmol) and triethylamine (150 mg, 1.5 mmol) were dissolved in dichloromethane (20 mL). 4-fluoro-3-(fluoromethyl)aniline (175 mg, 1.22 mmol) was added to the mixture at 0 C. The mixture was stirred at 10C for 30 minutes. The mixture was used to the next step without further purification.Triethylamine (152 mg, 1.5 mmol) and 3-methyl-3-oxetanamine (131 mg. 1.5 mmol) were added to the above obtained reaction mixture at 0 C. The mixture was stirred at 20 C for 1 hour. The solvent was removed in vacuo and the obtained residue was purified by reversed phase high performance liquid chromatography (Column: Gemini 25020mm5um.. A: H2O+0.1%TFA B: MeCN. 27% to 57% B in A). The product fractions were collected and the organic solvent was removed in vacuo. The fraction was neutralized by saturated NaHC03. The mixture was extracted with dichloromethane (3 x 20 mL) and the combined organic layer was dried over Na2S04 and concentrated in vacuo, resulting in compound 127 (91.1 mg). Method A; Rt: 4.95 min. m/z : 397.3 (M+H)+ Exact mass: 396.1. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.41 (s, 3 H) 4.14 (d, J=6.3 Hz, 2 H) 4.56 (d, J=6.3 Hz, 2 H) 5.52 (d, J=48 Hz, 2 H) 7.31 (t, J=9.4 Hz, 1 H) 7.72 - 7.89 (m, 2 H) 7.92-7.97 (m, 1 H) 8.03 (d, J=8.0 Hz, 1 H) 8.23 (d, J=7.8 Hz, 1 H) 8.39 (s, 1 H) 8.55 (s, 1 H) 10.67 (s, 1 H).

Reference： [1]Australian Journal of Chemistry,1977,vol. 30,p. 1611 - 1615
[2]Patent: WO2013/96744,2013,A1 .Location in patent: Page/Page column 226
[3]Patent: WO2014/33170,2014,A1 .Location in patent: Page/Page column 69; 70
[4]Patent: WO2014/33176,2014,A1 .Location in patent: Page/Page column 69-70

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[ CAS No. 63878-68-2 ] {[proInfo.proName]}

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[ 63878-68-2 ] Synthesis Path-Upstream 1~3

[ 63878-68-2 ] Synthesis Path-Downstream 1~1

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