4225-92-7|2-Bromo-1-mesitylethanone| Ambeed

CAS No. :	4225-92-7
Formula :	C₁₁H₁₃BrO
M.W :	241.12
SMILES Code :	CC1=CC(C)=CC(C)=C1C(CBr)=O
MDL No. :	MFCD00227709
InChI Key :	HRAZXKYOYNRVMU-UHFFFAOYSA-N
Pubchem ID :	219480

Safety of [ 4225-92-7 ]

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

Application In Synthesis of [ 4225-92-7 ]

* 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 [ 4225-92-7 ]

[ 4225-92-7 ] Synthesis Path-Downstream 1~55

1
[ 110-91-8 ]
[ 4225-92-7 ]
[ 102004-60-4 ]

References: [1]Journal of the American Chemical Society,1956,vol. 78,p. 4135,4138.

2
[ 110-86-1 ]
[ 4225-92-7 ]
[ 26031-76-5 ]

References: [1]Chemische Berichte,1937,vol. 70,p. 864,875.

3
[ 108-89-4 ]
[ 4225-92-7 ]
4-methyl-1-(2,4,6-trimethyl-phenacyl)-pyridinium; bromide [ No CAS ]

References: [1]Journal of the American Chemical Society,1953,vol. 75,p. 2330,2331.

4
[ 39603-24-2 ]
[ 4225-92-7 ]
3-hydroxy-2-mesityl-6,8-dimethyl-quinoline-4-carboxylic acid [ No CAS ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1932,vol. <2> 133,p. 259,268.

5
[ 60-29-7 ]
[ 4225-92-7 ]
[ 925-90-6 ]
[ 1667-01-2 ]

References: [1]Journal of the American Chemical Society,1932,vol. 54,p. 3665,3672.

6
[ 1667-01-2 ]
[ 4225-92-7 ]

Yield	Reaction Conditions	Operation in experiment
	With bromine; In water; acetic acid;	PREPARATION I 2-bromo-1-(2,4,6-trimethylphenyl)-1-ethanone (Compound 1) Dissolve 0.3 mol of 1-(2,4,6-trimethylphenyl)-1-ethanone in 200 ml of glacial acetic acid, and add 31.8 g of bromine dropwise while maintaining the reaction medium at a temperature below 10 C. When the addition is complete, allow the reaction medium to return to room temperature and leave at this temperature for 2 hours. Then pour the reaction medium into 500 ml of ice-cold water and extract the aqueous phase with ethyl ether. Wash the organic extracts with saturated aqueous sodium bicarbonate solution and then with salt water, and dry over anhydrous magnesium sulphate. After evaporation of the solvent, an oil is obtained, which may be used without further purification.
	With copper(ll) bromide; In ethyl acetate; for 1.5h;Reflux;	Synthesis of Exemplary Aminothiazoles and the Related Intermediates2-Bromo-1-mesitylethanone. To a solution of 1-mesitylethanone (1.02 g, 6.27 mmol) in EtOAc (50 mL) was added copper(II) bromide (CuBr2, 2.85 g, 12.8 mmol). The reaction mixture was heated at reflux for 90 min. The solution was allowed to cool down, and the resultant solids were filtered off and washed with EtOAc. The filtrate was concentrated under reduced pressure to give crude 2-bromo-1-mesitylethanone (1.67 g) as yellow oil: 1H NMR (500 MHz, CDCl3) delta 6.87 (2H, s), 4.27 (2 H, s), 2.31 (3H, s), 2.22 (6H, s).
	With copper(ll) bromide; In ethyl acetate; for 1.5h;Reflux;	To a solution of 1-mesitylethanone (1.02 g, 6.27 mmol) in EtOAc (50 mL) was added copper(II) bromide (CuBr2, 2.85 g, 12.8 mmol). Thereaction mixture was heated at reflux for 90 mm. The solution was allowed to cool down, andthe resultant solids were filtered off and washed with EtOAc. The filtrate was concentrated under reduced pressure to give crude 2-bromo-1-mesitylethanone (1.67 g) as yellow oil: 1H NMR (500 MHz, CDCl3) delta 6.87 (s, 2 H), 4.27 (s, 2H), 2.31 (s, 3 H), 2.22 (s, 6 H).

References: [1]Patent: EP1215208,2002,A2 .Location in patent: Example C(57).
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 4098 - 4110.
[3]Journal of the American Chemical Society,1984,vol. 106,p. 2630 - 2636.
[4]Journal of the Chemical Society. Chemical communications,1981,p. 1016 - 1017.
[5]Journal fur praktische Chemie (Leipzig 1954),1932,vol. <2> 133,p. 259,267 Anm. 2.
[6]Journal of the American Chemical Society,1939,vol. 61,p. 2362,2363.
[7]Tetrahedron Letters,1989,vol. 30,p. 5163 - 5166.
[8]Journal of the American Chemical Society,1984,vol. 106,p. 2630 - 2636.
[9]Patent: US5464847,1995,A .
[10]Journal of Organometallic Chemistry,2010,vol. 695,p. 2118 - 2125.
[11]Patent: US2011/230486,2011,A1 .Location in patent: Page/Page column 9.
[12]Patent: WO2013/82324,2013,A1 .Location in patent: Paragraph 00263.
[13]Tetrahedron Letters,2013,vol. 54,p. 7175 - 7179.

7
[ 4225-92-7 ]
[ 91-56-5 ]
3-hydroxy-2-mesityl-quinoline-4-carboxylic acid [ No CAS ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1932,vol. <2> 133,p. 259,268.

8
[ 598-21-0 ]
[ 108-67-8 ]
[ 4225-92-7 ]

Yield	Reaction Conditions	Operation in experiment
	With aluminum (III) chloride; In dichloromethane; at 0 - 5℃;	General procedure: (ii)To a stirred solution ofAlCl3 (12 mmol, 3.0 equiv.) in dichloromethane(10 mL) was added 8m or 8n(4 mmol, 1.0 equiv.) at 0 . Then a solution of2-bromoacetyl bromide (8 mmol, 2.0 equiv.) in dichloromethane (5 mL) was added dropwisein a period of 10 min. The reaction mixture was stirred at 0~5 for additional 15~30 min. After that, carefully added theNaHCO3 until pH > 7 and extracted with dichloromethane (3*15mL).The combined organic layers were dried over anhydrous Na2SO4and concentrated in vacuo to affordcrude product 2-bromo-1-arylethanone 9m or 9n as yellow solid, which directly using for next step.

References: [1]Journal of Biological Chemistry,1915,vol. 21,p. 445.
[2]MedChemComm,2015,vol. 6,p. 1036 - 1042.
[3]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 3669 - 3674.

9
[ 4225-92-7 ]
[ 108-95-2 ]
[ 60904-57-6 ]

References: [1]Journal of the American Chemical Society,1953,vol. 75,p. 3177.

10
[ 532-32-1 ]
[ 4225-92-7 ]
[ 65080-42-4 ]

References: [1]Bulletin of the Chemical Society of Japan,1977,vol. 50,p. 2686 - 2688.

11
[ 4225-92-7 ]
[ 23722-23-8 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1969,vol. 311,p. 604 - 613.

12
[ 288-32-4 ]
[ 4225-92-7 ]
α-imidazolyl-(2,4,6-trimethylacetophenone) [ No CAS ]

References: [1]Pharmaceutical Chemistry Journal,1990,vol. 23,p. 847 - 849.

13
[ 616-47-7 ]
[ 4225-92-7 ]
[ 121704-64-1 ]

References: [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2301 - 2306.

14
[ 1667-01-2 ]
[ 4225-92-7 ]
[ 408511-50-2 ]

References: [1]Journal of the Chemical Society. Chemical communications,1989,p. 1548 - 1549.

15
[ 4225-92-7 ]
[ 3887-61-4 ]
2-(4-Fluoro-phenylsulfanyl)-1-(2,4,6-trimethyl-phenyl)-ethanone [ No CAS ]