3-(2-Dimethylaminoethoxy)-bromobenzene

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3-(2-Dimethylaminoethoxy)-bromobenzene Basic information
Product Name:3-(2-Dimethylaminoethoxy)-bromobenzene
Synonyms:[2-(3-BROMO-PHENOXY)-ETHYL]-DIMETHYL-AMINE;UKRORGSYN-BB BBV-070799;2-(3-BroMophenoxy)-N,N-diMethylethanaMine;Ethanamine, 2-(3-bromophenoxy)-N,N-dimethyl-;2-(3-bromophenoxy)-n,n-dimethylethan-1-amine;3-(2-Dimethylaminoethoxy)-bromobenzene
CAS:221915-84-0
MF:C10H14BrNO
MW:244.13
EINECS:
Product Categories:
Mol File:221915-84-0.mol
3-(2-Dimethylaminoethoxy)-bromobenzene Structure
3-(2-Dimethylaminoethoxy)-bromobenzene Chemical Properties
Boiling point 280.0±20.0 °C(Predicted)
density 1.309±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
pka8+-.0.28(Predicted)
AppearanceColorless to light yellow Liquid
Safety Information
MSDS Information
3-(2-Dimethylaminoethoxy)-bromobenzene Usage And Synthesis
Synthesis
2-Dimethylaminoethanol

108-01-0

3-Bromophenol

591-20-8

3-(2-DIMETHYLAMINOETHOXY)-BROMOBENZENE

221915-84-0

Diisopropyl diisopropyl diisopropyl-1,2-dicarboxylate (1.56 g, 7.34 mmol) was slowly added dropwise to a solution of THF (20 mL) containing 3-bromophenol (1.155 g, 6.68 mmol), 2-(dimethylamino)ethanol (0.65 g, 7.34 mmol) and triphenylphosphine (1.93 g, 7.34 mmol) at 0 °C. The reaction mixture was gradually warmed to room temperature over a period of 16 h. The volatiles were subsequently removed by distillation under reduced pressure. The residue was dissolved in ethyl acetate (20 mL) and extracted with 1N HCl (20 mL), the aqueous phase was retained and washed with ethyl acetate. The aqueous phase was subsequently neutralized with saturated NaHCO3 solution (50 mL), extracted again with ethyl acetate, and the organic phase was dried over anhydrous MgSO4. Finally, the target product 2-(3-bromophenoxy)-N,N-dimethylethylamine (1.03 g, 63% yield) was purified by silica gel column chromatography (eluent: 4% MeOH/DCM) as an oil.

References[1] Patent: WO2009/111279, 2009, A1. Location in patent: Page/Page column 93
3-(2-Dimethylaminoethoxy)-bromobenzene Preparation Products And Raw materials
Raw materials2-Dimethylaminoethanol-->1,3-Dibromobenzene-->3-Bromophenol-->Tetrahydrofuran-->Diisopropyl azodicarboxylate-->Triphenylphosphine
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