2-BROMO-1-(2-THIENYL)-1-PROPANONE synthesis

Yield:75815-46-2 95.9%

Reaction Conditions:

with phenyltrimethylammonium tribromide in dichloromethane; for 12 h;Reflux;

Steps:

2-Bromo-1-(thiophen-2-yl) propan-1-one (3):

PTT (37.6 g, 0.1 mol) was added to a solution of compound 2 (14 g, 0.1 mol) in dichloromethane (150 mL) and the mixture was heated under reflux for 12 h. After cooling to room temperature, the reaction mixture was neutralised with aqueous potassium carbonate solution and extracted with dichloromethane (3×50 mL). The organic layer was washed with water (100 mL) and brine (100 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give (3) as pale yellow oil (21.1g, 95.9%), (lit.¹⁴ pale yellow oil). IR (cm^-1): 3103, 2978, 2925, 2862, 1664, 1517, 1441, 1413, 1376, 1355, 1246, 1167, 1064, 985, 942, 903, 855, 724, 648, 585, 566, 538; ¹H NMR (300 MHz, CDCl₃) δ 1.84-1.94 (m, 3H), 5.12-5.18 (m, 1H), 7.14-7.17 (m, 1H), 7.68-7.70 (m, 1H), 7.83-7.85 (m, 1H); ¹³C NMR (75 MHz, CDCl₃) δ 20.27, 42.42, 128.23, 133.02, 134.81, 140.76, 186.73; MS m/z: 219.0 ([M-H]⁺, 100%), 221.0 ([M+H]⁺, 100%).

References:

Zhang, Shuguang;Huang, Shuang;Feng, Chengliang;Cai, Jin;Chen, Junqing;Ji, Min [Journal of Chemical Research,2013,vol. 37,# 7,p. 406 - 408]