Bromine → [2-(3-Bromo-benzo[b]thiophen-2-yl)-ethyl]-dimethyl-amine

HRID 746602Notes

Reaction equation

HRID 746602 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

HCID 24408BromineHCID 58591561HCID 58591561, compound

Product 1

HCID 58591562[2-(3-Bromo-benzo[b]thiophen-2-yl)-ethyl]-dimethyl-amine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

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.

Workup

  1. washsubsequently washed with sat. NaHCO3 (3×) and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified by silica gel column chromatography in EtOAc

Sources & evidence

ORD record
ord-b79a5c31d8ab488cb5678e9d050a05f3
Source dataset
uspto-grants-2008_07
Patent number
US07393865B2

Reaction notes

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