1332392-76-3|5-Bromo-2-chloro-3-(difluoromethyl)pyridine| Ambeed

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Quality Control of [ 1332392-76-3 ] Purity: 98% SDS Specification

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Product Details of [ 1332392-76-3 ]

CAS No. :	1332392-76-3
Formula :	C₆H₃BrClF₂N
M.W :	242.45
SMILES Code :	FC(C1=CC(Br)=CN=C1Cl)F
MDL No. :	MFCD22199307
InChI Key :	SENZWWWZWMAPAI-UHFFFAOYSA-N
Pubchem ID :	60623016

Safety of [ 1332392-76-3 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H301-H311-H331
Precautionary Statements:	P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501
Class:	6.1
UN#:	2810
Packing Group:	Ⅲ

Application In Synthesis of [ 1332392-76-3 ]

* 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 [ 1332392-76-3 ]

[ 1332392-76-3 ] Synthesis Path-Downstream 1~1

1
[ 228251-24-9 ]
[ 1332392-76-3 ]

Yield	Reaction Conditions	Operation in experiment
87%	With diethylamino-sulfur trifluoride; In ethanol; dichloromethane; at 25℃; for 2.25h;	To a solution of step-1 intermediate (4.79 g, 21.73 mmol) in DCM (125 mL) was added catalytic amount of ethanol (0.127 mL, 2.173 mmol) followed by the addition of DAST (5.74 mL, 43.5 mmol) dropwise at 25eC for 15 min. Reaction mixture was stirred at same temperature for 2h before quenching with aqueous saturated solution of NaHCC at OeC. The layers were separated and the aqueous layer was washed with DCM. Combined organic layer was washed with brine, dried over Na2SC>4 and concentrated in vaccum and the crude product was purified by flash column chromatography (silica gel) to afford 4.60 g (87%) of the titled compound. 1HNMR (400 MHz, DMSO-d6) \|\|8.79 (d, J = 2.5 Hz, 1H), 8.42 (d, J = 2.5 Hz, 1H), 7.21 (t, J = 53.5 Hz, 1H); GCMS (m/z) 240.85 (M)+.
	With diethylamino-sulfur trifluoride;ethanol; In dichloromethane; at 20℃; for 2h;	To a solution of <strong>[228251-24-9]5-bromo-2-chloronicotinaldehyde</strong> (5.05 g, 23.2 mmol) in DCM (30 niL), were added ethanol (0.13 mL, 2.32 mmol) and DAST (7.51 g, 46.4 mmol) at room temperature. The resulting mixture was stirred for 2h at that temperature. To the reaction mixture was slowly added saturated aqueous sodium bicarbonate (100 mL). The organic layer was separated, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (0 to 50% EtOAc in petroleum ether) to afford 3.80 g of 5-bromo-2-chloro-3-(difluoromethyl)pyridine. LCMS [M+H]+ 243.1.
	With diethylamino-sulfur trifluoride; In ethanol; dichloromethane; at 20℃; for 2h;Inert atmosphere;	To 5-bromo-2-choronicotinadehyde (296 g, 12.8 mmo) in DCM (75 mD under N2 atmosphere were added EtOH (0075 m, 1.27 mmo) and dropwise over 5 mm DAST (3.74 mL 25.5 mmoD at RT. The reaction mixture was stirred at RT for 2h. After coong to 0C, the reaction mixture was quenched with aqueous saturated NaHCO3, the organic phase was separated and the aqueous phase was extracted with DCM. The combined organic phases were washed with water, brine and dried over Na2SO4, fUtered and evaporated to dryness to afford 5-bromo-2-choro-3-(difluoromethy)pyridine. Rt = 1.02 mm (UPLC Method 82), H NMR (400 MHz, DM80-cl6) O ppm: 8.78 (d, IH), 8.40 (d, IH), 7.13 (t, IH), 19F NMR (400 MHz, DM80 d6) : O ppm: .117.021-116,88 (d, 2F).

References: [1]Patent: WO2018/20474,2018,A1 .Location in patent: Page/Page column 157.
[2]Patent: WO2011/103202,2011,A2 .Location in patent: Page/Page column 181.
[3]Patent: WO2015/181747,2015,A1 .Location in patent: Page/Page column 76; 77.

Historical Records

Technical Information

• Alkyl Halide Occurrence • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Preparation of Amines • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

Related Functional Groups of
[ 1332392-76-3 ]

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Difluoromethyls

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Related Parent Nucleus of
[ 1332392-76-3 ]

Pyridines

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CAS No.: 1332392-76-3

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