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Citations (30)
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1
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Rx-ID: 304856 Find similar reactions
96%
With aluminum (III) chloride; bromine in diethyl ether
T=0°C;
Mayer; Wimmer; Dillon-Carter; Partilla; Burchardt; Mihovilovic; Baumann; Sitte
British Journal of Pharmacology, 2016 , p. 2657 - 2668 Title/Abstract Full Text View citing articles Show Details
95%
With bromine in hexane; water; acetic acid; ethyl acetate
McConnell, Robert Ivan; Benchikh, Elouard; Lowry, Philip Andrew; Fitzgerald, Stephen Peter
Patent: US2012/94316 A1, 2012 ;
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Title/Abstract Full Text Show Details
1.i:i) i) α-bromo-4-methylpropiophenone 4-Methylpropiophenone (30 g, 0.202 mol) in acetic acid (100 ml) was added to a solution of Bromine (34 g, 1.05 eq) in acetic acid (100 ml) dropwise. The mixture was stirred at RT for 4 h. The acetic acid was removed in vacuo. To the residue was added water (100 ml) and extracted with dichloromethane (3*200 ml). Extracts were combined and washed with sat. sodium bicarbonate solution (200 ml), dried over sodium sulphate, filtered and evaporated to dryness. The crude was purified by column chromatography (silica gel: 20percent ethyl acetate in hexane) to give the title compound (43.9 g, 95percent) as a yellow oil.
89%
With bromine; acetic acid
T=30°C;
Gregg, Ryan A.; Baumann, Michael H.; Partilla, John S.; Bonano, Julie S.; Vouga, Alexandre; Tallarida, Christopher S.; Velvadapu, Venkata; Smith, Garry R.; Peet, M. Melissa; Reitz, Allen B.; Negus, S. Stevens; Rawls, Scott M.
British Journal of Pharmacology, 2015 , vol. 172, # 3 p. 883 - 894 Title/Abstract Full Text View citing articles Show Details
78%
With N-Bromosuccinimide; ureahydrogen peroxide; 1-butyl-3methylimidazolium Tetrafluoroborate
T=60°C;
Lee, Jong Chan; Park, Hyun Jung
Synthetic Communications, 2007 , vol. 37, # 1 p. 87 - 90 Title/Abstract Full Text View citing articles Show Details
54%
With bromine in acetic acid
T=30°C; 2 h;
Uemura, Sakae; Fukuzawa, Shin-ichi; Yamauchi, Takayoshi; Hattori, Kaneaki; Mizutaki, Shoichi; Tamaki, Kentaro
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1986 , p. 1983 - 1987 Title/Abstract Full Text View citing articles Show Details
With bromine; benzene
Sanchez
Bulletin de la Societe Chimique de France, 1929 , vol. <4> 45, p. 284 Full Text View citing articles Show Details
With bromine in diethyl ether
Villa; Taddei; Ferri
Il Farmaco; edizione scientifica, 1974 , vol. 29, # 1 p. 73 - 79 Title/Abstract Full Text View citing articles Show Details
With bromine
Schmauder; Groeger; Schwalbe
Die Pharmazie, 1969 , vol. 24, # 12 p. 735 - 745 Title/Abstract Full Text View citing articles Show Details
With bromine in acetic acid
Uemura, Sakae; Fukuzawa, Shin-ichi; Yamauchi, Takayoshi; Hattori, Kaneaki; Mizutaki, Shoichi; Tamaki, Kentaro
Journal of the Chemical Society, Chemical Communications, 1984 , # 7 p. 426 - 427 Title/Abstract Full Text View citing articles Show Details
With bromine in dichloromethane; water
T=35°C;
Kalendra, Diane M.; Sickles, Barry R.
Journal of Organic Chemistry, 2003 , vol. 68, # 4 p. 1594 - 1596 Title/Abstract Full Text View citing articles Show Details
With bromine in aluminium chloride; chloroform
Synthelabo
Patent: US4690931 A1, 1987 ;
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Title/Abstract Full Text Show Details
12:2-Bromo-4'-methylpropiophenone
EXAMPLE 12 2-Bromo-4'-methylpropiophenone 14.8 g (0.1 mol) of 4'-methylpropiophenone are introduced into 100 ml of chloroform, in the presence of a small amount of finely ground aluminium chloride, and a solution of 15.9 g (0.1 mol; 5 ml) of bromine, in 20 ml of chloroform is added dropwise whilst cooling with an ice bath. The mixture is left to react overnight at ambient temperature. It is then filtered, the solvent is evaporated off from the filtrate and the crystalline residue is washed with diethyl ether. 21.5 g of crystals are collected.
6.33 g
With bromine
T=0 - 20°C;
Watanabe, Kazutoshi; Morinaka, Yasuhiro; Hayashi, Yoshio; Shinoda, Masaki; Nishi, Hiroyoshi; Fukushima, Nobuko; Watanabe, Toshiaki; Ishibashi, Akira; Yuki, Satoshi; Tanaka, Masahiko
Bioorganic and Medicinal Chemistry Letters, 2008 , vol. 18, # 4 p. 1478 - 1483 Title/Abstract Full Text View citing articles Show Details
With bromine in dichloromethane
10 h; Inert atmosphere;
Carroll, F. Ivy; Blough, Bruce E.; Abraham, Philip; Mills, Andrew C.; Holleman, J. Ashley; Wolckenhauer, Scott A.; Decker, Ann M.; Landavazo, Antonio; McElroy, K. Timothy; Navarro, Hernan A.; Gatch, Michael B.; Forster, Michael J.
Journal of Medicinal Chemistry, 2009 , vol. 52, # 21 p. 6768 - 6781 Title/Abstract Full Text View citing articles Show Details
With bromine in dichloromethane
10 h; Inert atmosphere; Hide Experimental Procedure
RESEARCH TRIANGLE INSTITUTE; CARROLL, Frank Ivy; BLOUGH, Bruce; ABRAHAM, Philip
Patent: WO2010/121022 A1, 2010 ; Location in patent: Page/Page column 68 ;
Title/Abstract Full Text Show Details
1.a.1: Synthesis of 2-(N-ferf-Butylamino)-4'-metb.ylpropiophenone (2h)Step 1. 2-Bromo-4'-methylpropiophenone (1Oh). 4'-Methylpropiophenone 9h (4.0 g, 0.027 mol) and methylene chloride (100 mL) were placed in a 250-mL flask equipped with a magnetic stir bar. The solution was stirred under N2 and bromine (1.38 mL, 27.0 mmol) was syringed into flask. (Note: a small amount of bromine was added to initiate the reaction; the color dissipated as the reaction occurs; after the reaction initiated, the remaining bromine was added over 10 min.) A needle was placed in the septa to allow the hydrogen bromide gas formed in the reaction to escape from the flask. After stirring for 1O h, saturated sodium bicarbonate solution was added to basify the reaction. When the pH was 9, the aqueous layer was extracted with methylene chloride. The organic layer was dried (Na2SO4) and filtered. The solvent was removed under reduced pressure to give 6.33 g of 1Oh as a white solid. 1H NMR (CDCl3) δ 7.94-7.89 (d, 2H), 7.30-7.25 (d, 2H), 5.33-5.23 (q, IH), 2.42 (s, 3H), 1.91-1.87 (d, 3H). With bromine in dichloromethane
T=20°C; 0.5 h;
Blough, Bruce E.; Landavazo, Antonio; Partilla, John S.; Baumann, Michael H.; Decker, Ann M.; Page, Kevin M.; Rothman, Richard B.
ACS Medicinal Chemistry Letters, 2014 , vol. 5, # 6 p. 623 - 627 Title/Abstract Full Text View citing articles Show Details
With bromine in dichloromethane
T=20°C; Inert atmosphere;
Chen, Jiajia; Guo, Wei; Wang, Zhenrong; Hu, Lin; Chen, Fan; Xia, Yuanzhi
Journal of Organic Chemistry, 2016 , vol. 81, # 13 p. 5504 - 5512 Title/Abstract Full Text View citing articles Show Details
With bromine in diethyl ether
T=20°C; Inert atmosphere;
Wen, Genfa; Su, Yingpeng; Zhang, Guoxiang; Lin, Qiqiao; Zhu, Yujin; Zhang, Qianqian; Fang, Xinqiang
Organic Letters, 2016 , vol. 18, # 16 p. 3980 - 3983 Title/Abstract Full Text View citing articles Show Details
With N-Bromosuccinimide; toluene-4sulfonic acid in acetonitrile
T=60°C; 4 h;
Wu, Weilong; You, Cai; Yin, Congcong; Liu, Yuanhua; Dong, Xiu-Qin; Zhang, Xumu
Organic Letters, 2017 , vol. 19, # 10 p. 2548 - 2551 Title/Abstract Full Text View citing articles Show Details
2
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With [hydroxy(tosyloxy)iodo]benzene; toluene4-sulfonic acid in acetonitrile T=20°C; 120 h; Inert atmosphere;
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Rx-ID: 41668275 Find similar reactions
Jobin-Des Lauriers, Antoine; Legault, Claude Y.
Organic Letters, 2016 , vol. 18, # 1 p. 108 - 111 Title/Abstract Full Text View citing articles Show Details
3
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Rx-ID: 7363037 Find similar reactions
CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; DAVIOUD-CHARVET, Elisabeth; LANFRANCHI, Don Antoine; JOHANN, Laure; WILLIAMS, David Lee; CESAR RODO, Elena
Patent: WO2012/131010 A1, 2012 ;
Location in patent: Page/Page column 78 ; Title/Abstract Full Text Show Details
99%
With bromine in acetic acid
T=20°C; Hide Experimental Procedure
Centre National de la Recherche Scientifique; Davioud-Charvet, Elisabeth; Lanfranchi, Don Antoine; Johann, Laure; Williams, David Lee
Patent: EP2505583 A1, 2012 ; Location in patent: Paragraph 0116-0118 ; Title/Abstract Full Text Show Details
5.2:EXAMPLE 5: General procedure for alpha-bromination of propiophenone
General procedure: It is based on the work from S. Uemura & S.-I. Fukuzawa J. Chem. Soc., Pekin Trans. I, 1986, 1983-1987 [0111] To a stirred solution of propiophenone in acetic acid (1 eq, 2.45 mmol.mL-1) was added dropwise bromine/AcOH (1 eq, 20 mmol.mL-1) keeping the temperature below 20°C. The reaction mixture was stirred at R.T. for 1-2h, during which period the orange/red color of the mixture turned yellowish. The reaction mixture was poured in 10 volumes of water. The precipitated solids was filtered, washed with water and dried and directly used as such in the next step. (Note: sometimes the bromo compounds may not crystallize, the aqueous phase should then be extracted with an organic solvent such as dichloromethane). Yield : >98percent (colorless oil, LACRYMATORY..) [0114] 1H NMR (200 MHz, CDCl3) : δ = 1.90 (d, J = 6.6Hz, 3H), 5,25 (q, J = 6.6 Hz, 1H), 7.16 (mc, 2H), 8.06 (dd, J = 8.7 Hz, JH-F = 5.4 Hz, 2H) ppm [0115] Due to its lacrymatory nature the crude was directly engaged in the next step (6.1). KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; JEIL PHARMACEUTICAL CO., LTD.
Patent: WO2005/92896 A1, 2005 ; Location in patent: Page/Page column 28; 31 ;
79%
Title/Abstract Full Text Show Details
Dombrowskii et al.
J. Gen. Chem. USSR (Engl. Transl.), 1962 , vol. 32, p. 2278,2246 Full Text Show Details
Szotyori et al.
Revue Roumaine de Chimie, 1964 , vol. 9, p. 545,554 Full Text Show Details
Szotyori et al.
Revue Roumaine de Chimie, 1967 , vol. 12, p. 1155,1167 Full Text Show Details
Shur; Barba
Izvestiya Akademii Nauk Moldavskoi SSR, 1967 , p. 70 Chem.Abstr., 1969 , vol. 70, # 19740h Full Text Show Details
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Tsuda; Masami; Tanaka; Mitsushi; Nakamura; Ayatsugu
Patent: US5998459 A1, 1999 ; Title/Abstract Full Text Show Details
The following compounds were synthesised by substantially the same procedure as Reference Example 1. ... 2-Bromo-2',5'-dichloropropiophenone, 2-Bromo-3'-nitroacetophenone, 2-Bromo-1-(2-pyridyl)-1-propanone, 2-Bromo-1-(2-naphthyl)-1-propanone, 2-Bromo-4'-methylpropiophenone, 2-Bromo-1-(3-pyridyl)-1-propanone, 2-Bromo-1-(2-thienyl)-1-propanone, 2-Bromo-3',4'-dichloropropiophenone, ...
4
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5
Multi-step reaction with 2 steps 1: AlCl3 / petroleum ether 2: Br2
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With 1,4-dioxane; hydrogen bromide
Schmauder; Groeger; Schwalbe
Die Pharmazie, 1969 , vol. 24, # 12 p. 735 - 745 Title/Abstract Full Text View citing articles Show Details
Rx-ID: 7363038 Find similar reactions
Wilds; Meader
Journal of Organic Chemistry, 1948 , vol. 13, p. 763,773 Full Text View citing articles Show Details
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Rx-ID: 7363040 Find similar reactions
7
Rx-ID: 22674456 Find similar reactions
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6
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Sanchez
Bulletin de la Societe Chimique de France, 1929 , vol. <4> 45, p. 284 Full Text View citing articles Show Details
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Rx-ID: 749462 Find similar reactions
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With carbon disulfide; aluminium trichloride
Kunckell
Chem. Zentralbl., 1912 , vol. 83, # I p. 1557 Full Text Show Details
8
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Rx-ID: 7363039 Find similar reactions
With carbon disulfide; aluminium trichloride
Kunckell
Chem. Zentralbl., 1912 , vol. 83, # I p. 1557 Full Text Show Details
With aluminium trichloride
Collet
Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1897 , vol. 125, p. 306 Full Text View citing articles Show Details