Bromine → [2-(3-Bromo-benzo[b]thiophen-2-yl)-ethyl]-dimethyl-amine
Reaction equation
[S:1]1[C:5]([CH2:6][CH2:7][N:8]([CH3:10])[CH3:9])=[CH:4][C:3]2[CH:11]=[CH:12][CH:13]=[CH:14][C:2]1=2.[Br:15]Br>C(Cl)(Cl)Cl>[Br:15][C:4]1[C:3]2[CH:11]=[CH:12][CH:13]=[CH:14][C:2]=2[S:1][C:5]=1[CH2:6][CH2:7][N:8]([CH3:10])[CH3:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a cooled solution of Compound 1a (2-Benzo[b]thiophen-2-yl-ethyl) -dimethyl-amine (39 mmol) in chloroform (500 mL) was added Br2 (43 mmol) dropwise. The mixture was stirred overnight at RT and subsequently washed with sat. NaHCO3 (3×) and brine, dried (MgSO4) and concentrated in vacuo. The crude material was purified by silica gel column chromatography in EtOAc to afford [2-(3-Bromo-benzo[b]thiophen-2-yl)-ethyl]-dimethyl-amine, Compound 2a, as an oil (9.6 g, 86%); MS (MH+) 283.9.