Toluene → [3-(4-bromophenoxy)propyl]dimethylamine

HRID 2120932Notes

Reaction equation

HRID 2120932 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl.[CH3:10][N:11]([CH3:15])[CH2:12][CH2:13]Cl.[C:16]1(C)C=CC=CC=1>[OH-].[Na+]>[CH3:10][N:11]([CH2:12][CH2:13][CH2:16][O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[CH3:15]

Participants

5

Reactant 3

HCID 1140TolueneHCID 78084-BromophenolHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 2183674[3-(4-bromophenoxy)propyl]dimethylamine

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

4-bromophenol (5.0 g, 28.9 mmol) and 2-dimethylaminoethyl chloride hydrochloride (4.6 g, 31.8 mmol) were combined in a mixture of toluene (100 mL) and 1 M NaOH (50 mL) and heated at reflux for 16 h. The layers were separated and the organic phase was washed with 1 M NaOH, dried (MgSO4) and concentrated to yield 4.2 g of the title compound as a yellow oil which was used without further purification. 1H NMR (400 MHz, CDCl3): δ 2.34 (6H, s), 2.72 (2H, t), 4. 01 (2H, t), 6.73 (2H, m), 7.33 (2H, m).

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 h
  3. customThe layers were separated
  4. washthe organic phase was washed with 1 M NaOH
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b5d840c0cc7d44b88e06198df65a1fca
Source dataset
uspto-grants-2004_02
Patent number
US06693137B1

Reaction notes

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