2-(2-Bromoacetyl)thiophene

Chemical Properties

white to light yellow crystal powde

Synthesis

Example 1.12: Synthesis of 2-bromo-1-(thiophen-2-yl)ethan-1-one. A solution of bromine (2.53 g, 0.82 mL, 0.0158 mol) in dichloromethane (8 mL) was added dropwise to a solution of 2-acetylthiophene (2.0 g, 1.71 mL, 0.0158 mol) in dichloromethane (10 mL). The reaction mixture was stirred at 25 °C for 1 h and subsequently neutralized with saturated aqueous sodium bicarbonate solution. The organic layer was washed with water and dried. After evaporation of the solvent, the solid residue was purified by column chromatography (silica gel, eluent ethyl acetate:n-hexane = 5:95) to afford 2-bromo-1-(thiophen-2-yl)ethan-1-one as an oil (2.60 g, 80% yield). [Note: Alternative preparations of 1-(thiophen-2-yl)ethan-1-one have been reported recently, see: Ostrowski, T.; Golankiewicz, B.; De Clercq, E.; Andrei, G.; Snoeck, R. Synthesis and anti-VZV activity of tricyclic acyclovir and 9-{[cis-1',2'-bis(hydroxymethyl)cycloprop-1'-yl]methyl}guanine analogues as 6-heteroaryl derivatives. eur. J. Med. Chem. 2009, 44, 3313-3317.]

References

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[2] Synthetic Communications, 1996, vol. 26, # 6, p. 1083 - 1096
[3] Russian Journal of Organic Chemistry, 2001, vol. 37, # 9, p. 1210 - 1219
[4] ChemMedChem, 2018, vol. 13, # 11, p. 1102 - 1114
[5] Phosphorus, Sulfur and Silicon and the Related Elements, 2013, vol. 188, # 12, p. 1835 - 1844