O[CH2:2][C:3]#[C:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[BrH:13].O>C1(C)C=CC=CC=1>[Br:13][C:3]1[CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:6][CH:2]=1To a solution of 4-hydroxy-1-phenylbut-2-yn-1-one (3.2 g, crude) in toluene (60 mL) was added HBr (40%, 15 mL). The resulting solution was stirred for 40 min at 50° C. and then the reaction mixture was poured into water (300 mL), extracted with Et2O (4×100 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo to give a residue, which was purified by silica gel column chromatography (petroleum ether) to afford 4-bromo-2-phenylfuran as a yellow solid (1.3 g, 50%).
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