Water → [2-(3-Bromophenoxy)ethyl]dimethylamine

HRID 449148

Reaction equation

HRID 449148 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Cl.Cl[CH2:11][CH2:12][N:13]([CH3:15])[CH3:14].C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:11][CH2:12][N:13]([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 115633-BromophenolHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 413371[2-(3-Bromophenoxy)ethyl]dimethylamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Bromophenol (0.870 g, 5.00 mmol), (2-chloro-ethyl)-dimethylamine hydrochloride (0.792 g, 5.50 mmol) and Cs2CO3 (8 g, 25 mmol) were combined in DMF (20 mL) and the mixture was heated at reflux over night. H2O (20 mL) was added and the mixture was extracted with EtOAc, then washed with 2N NaOH and brine. The organic layers were combined, dried over Na2SO and concentrated to a brown oil which was then purified by flash chromatography (eluent: 20% EtOAc in hexanes).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux over night
  3. extractionthe mixture was extracted with EtOAc
  4. washwashed with 2N NaOH and brine
  5. dry with materialdried over Na2SO
  6. concentrationconcentrated to a brown oil which
  7. customwas then purified by flash chromatography (eluent: 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-7b6c563c346040629f1a39ef6f906e44
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Linked notes

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