26767-16-8|2-(2-Bromophenyl)-2-oxoacetic acid| Ambeed

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Quality Control of [ 26767-16-8 ] Purity: 95% SDS Specification

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Product Details of [ 26767-16-8 ]

CAS No. :	26767-16-8
Formula :	C₈H₅BrO₃
M.W :	229.03
SMILES Code :	OC(=O)C(=O)C1=CC=CC=C1Br
MDL No. :	MFCD00463413
InChI Key :	BCGITRTXBFIXCC-UHFFFAOYSA-N
Pubchem ID :	4241115

Safety of [ 26767-16-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 26767-16-8 ]

* 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 [ 26767-16-8 ]

[ 26767-16-8 ] Synthesis Path-Downstream 1~35

2
2-bromo-phenylglyoxylic acid amide [ No CAS ]
[ 26767-16-8 ]

References: [1]Chemische Berichte,1892,vol. 25,p. 3298.

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[ 2142-69-0 ]
[ 26767-16-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With pyridine; selenium(IV) oxide; at 100℃; for 2h;	8.3 g (75 mmoles) of selenium dioxide were added to 10 g (50 mmoles) of 2'- bromoacetophenone dissolved in 20 ml of pyridine; the mixture was left under magnetic stirring at 100C for 2 hours. After control in TLC and LC-MS, the mixture was filtered to eliminate the selenium and the pyridine was removed at reduced pressure. The residue was acidified with diluted HCl and extracted with ethyl acetate; the phases were then separated; the aqueous phase was re- extracted twice with ethyl acetate. The organic phases were joined and washed with water and a saturated solution of NaCl. After anhydrification on sodium sulfate, filtration and evaporation of the solvent at reduced pressure, 11.4 g of the desired product (50 mmoles) were obtained, as a cream-coloured solid. The raw product thus obtained was used for the subsequent reaction. Quantitative yield. LC-MS [M+H] = 229.
87%	With pyridine; selenium(IV) oxide; at 120℃; for 18h;Inert atmosphere;	Into a 250-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of l-(2-bromophenyl)ethan-l-one (10 g, 50.24 mmol, 1.00 equiv) in pyridine (80 mL). This was followed by the addition of Se02 (22 g, 198.27 mmol, 3.95 equiv). The resulting solution was stirred for 18 h at 120 C in an oil bath. The reaction mixture was cooled to room temperature. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was dissolved in 100 mL of water. The resulting mixture was washed with 2x50 mL of ethyl acetate. The pH value of the aqueous layer was adjusted to 1-2 with hydrogen chloride (4 mol/L). The resulting solution was extracted with 3x80 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. This resulted in 10 g (87%) of 2-(2- bromophenyl)-2-oxoacetic acid as yellow oil. MS (ESI) m/z 230 ([M + H]+)
	With pyridine; selenium(IV) oxide; at 90 - 110℃; for 5h;	General procedure: The substituted alpha-keto acids were prepared from oxidation of corresponding methyl ketones with SeO2 (Scheme 1). Methyl ketones (5 mmol), SeO2 (6 mmol), 20 mL of pyridine were added in a 50 mL round-bottom flask. The reaction mixture was stirred at 110 oC for 1 h, and under 90 oC for another 4 h. The desired products were isolated by silica-gel column chromatography.

References: [1]Patent: WO2017/168368,2017,A1 .Location in patent: Page/Page column 17.
[2]Patent: WO2014/143960,2014,A1 .Location in patent: Page/Page column 33.
[3]Tetrahedron,2007,vol. 63,p. 2695 - 2711.
[4]Chemical Communications,2013,vol. 49,p. 3640 - 3642.
[5]Advanced Synthesis and Catalysis,2013,vol. 355,p. 1517 - 1522.
[6]Tetrahedron Letters,2016,vol. 57,p. 2511 - 2514.
[7]European Journal of Organic Chemistry,2017,vol. 2017,p. 3830 - 3836.
[8]Advanced Synthesis and Catalysis,2017,vol. 359,p. 2390 - 2395.
[9]Organic and Biomolecular Chemistry,2017,vol. 15,p. 6592 - 6603.
[10]Tetrahedron Letters,2017,vol. 58,p. 4763 - 4765.
[11]Advanced Synthesis and Catalysis,2018,vol. 360,p. 4184 - 4190.
[12]Advanced Synthesis and Catalysis,2019,vol. 361,p. 1798 - 1802.
[13]Organic Letters,2020,vol. 22,p. 1442 - 1447.

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[ 26767-16-8 ]
(2-bromo-phenyl)-oxo-acetyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃;	General procedure: To a solution of alpha-ketoacids (1.0 eq., 0.5 M) in DCM was added a drop of DMF at room temperature followed by the addition of oxalyl chloride (1.2 eq.). The resulting mixture was stirred at this temperature until no gas was released. The reaction mixture was subsequently cooled to 0oC followed by the addition of amine (1.2 eq.) and Et3N (2.0 eq.). The resulting reaction mixture was warmed to room temperature and stirred for 4 h. After addition of water (5 mL), the mixture was washed with 1N HCl and water respectively and dried over Na2SO4. Purification by flash column chromatography afforded the desired alpha-ketoamides.

References: [1]Tetrahedron,2007,vol. 63,p. 2695 - 2711.
[2]Chemistry - A European Journal,2015,vol. 21,p. 9360 - 9363.
[3]Tetrahedron Letters,2017,vol. 58,p. 546 - 551.

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[ 26767-16-8 ]
[ 75-65-0 ]
[ 767288-73-3 ]