Water → 2-Bromo-3-[4-(2-ethylhexyl)-phenyl]-thiophene

Reaction equation

[CH2:1]([CH:3]([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:15]=[CH:14][S:13][CH:12]=2)=[CH:7][CH:6]=1)[CH3:2].C1C(=O)N([Br:27])C(=O)C1.O>CN(C)C=O>[Br:27][C:12]1[S:13][CH:14]=[CH:15][C:11]=1[C:8]1[CH:9]=[CH:10][C:5]([CH2:4][CH:3]([CH2:1][CH3:2])[CH2:16][CH2:17][CH2:18][CH3:19])=[CH:6][CH:7]=1

Participants

Procedure

A 250-mL round bottom flask was charged with 3-[4-(2-ethylhexyl)-phenyl]-thiophene (7 g, 0.026 mol), N,N-dimethyl formamide (DMF) (65 mL). The reaction mixture was stirred at ambient temperature for 5 minutes, whereupon a 0.4 M solution of NBS (0.026 mol) in DMF was added and the stirring continued for 2 hours. After addition of water, the mixture was extracted with diethyl ether (3×150 mL). The combined organic layer was dried over anhydrous magnesium sulfate (MgSO4). After the product was filtered, the solvent was removed by rotary evaporation. The crude product was purified using column chromatography on silica gel with hexane as the eluent (Rf=0.35). The compound was dried under vacuum to yield 8.7 g (95%) of slightly yellow oil.