| Identification | Back Directory | [Name]
1-Benzo[b]thiophen-3-yl-2-bromoethan-1-one | [CAS]
26167-45-3 | [Synonyms]
3-(Bromoacetyl)benzothiophene 3-(Bromoacetyl)benzo[b]thiophene 3-(Bromoacetyl)benzo[b]thiophene97% 3-(Bromoacetyl)benzo[b]thiophene 97% 1-Benzothiophen-3-yl-2-bromoethan-1-one Ethanone, 1-benzo[b]thien-3-yl-2-bromo- 1-(1-benzothiophen-3-yl)-2-bromoethanone 1-(Benzo[b]thiophen-3-yl)-2-broMoethanone 1-BENZO[B]THIOPHEN-3-YL-2-BROMOETHAN-1-ONE 1-(1-BENZOTHIOPHEN-3-YL)-2-BROMO-1-ETHANONE 1-(1-benzothiophen-3-yl)-2-broMoethan-1-one 1-Benzo[b]thiophen-3-yl-2-bromoethan-1-on, 97% 1-(Benzo[b]thiophen-3-yl)-2-bromoethan-1-one97% | [Molecular Formula]
C10H7BrOS | [MDL Number]
MFCD00176410 | [MOL File]
26167-45-3.mol | [Molecular Weight]
255.13 |
| Hazard Information | Back Directory | [Chemical Properties]
Gray solid | [Uses]
1-(Benzo[b]thiophen-3-yl)-2-bromoethanone is one of the thiazole analogs of indomethacin as selective COX-2 inhibitors. | [Synthesis]
General procedure for the synthesis of 1-benzo[b]thiophen-3-yl-2-bromoethyl-1-one from 1-(benzo[b]thiophen-3-yl)ethanone: 1-(benzo[b]thiophen-3-yl)ethanone (21 mmol) was dissolved in a mixed solvent of ethyl acetate (50 ml) and chloroform (50 ml), followed by addition of copper(II) bromide (40.2 mmol). The reaction mixture was stirred under reflux conditions for 3 hours. After completion of the reaction, the resulting copper bromide precipitate was removed by filtration. The filtrate was washed sequentially with distilled water (20 ml x 3) to remove water-soluble impurities and then dried with anhydrous sodium sulfate overnight. After drying, the desiccant was removed by filtration and the residue was washed with a small amount of ethyl acetate. The solvent in the filtrate was evaporated by rotary evaporator to obtain the crude product. Finally, the crude product was purified by ethanol recrystallization to give a light yellow crystalline solid in about 75% yield. | [References]
[1] Patent: EP2311828, 2011, A1. Location in patent: Page/Page column 9 [2] Tetrahedron Asymmetry, 2008, vol. 19, # 16, p. 1959 - 1964 [3] Patent: WO2014/31784, 2014, A1. Location in patent: Paragraph 0548 [4] Journal of Chemical Research, Miniprint, 1994, # 5, p. 1042 - 1059 [5] Journal of Scientific and Industrial Research, 1955, vol. 14 B, p. 11 |
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