Hydrochloric Acid → 2-(4-bromophenoxy)-N,N-diethylethanamine

HRID 1916515Notes

Reaction equation

HRID 1916515 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl[CH2:10][CH2:11][N:12]([CH2:15][CH3:16])[CH2:13][CH3:14].Cl.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][CH2:11][N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 13364Diethylaminoethyl chloride

Product 1

HCID 4239532-(4-bromophenoxy)-N,N-diethylethanamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 31.4 g (178 mmol) 4-bromophenol, 30.6 g (178 mmol) (2-chloro-ethyl)-diethyl-amine (used as the hydrochloride) and 61.5 g (445 mmol) K2CO3 in 300 mL DMF is heated to 80° C. for 8 h. The solvent is evaporated down i.vac., the residue combined with water, the aqueous phase exhaustively extracted with EtOAc, the combined organic phases washed with water again and dried over MgSO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, EtOAc/MeOH/NH3 90:10:1).

Workup

  1. customThe solvent is evaporated down i.vac
  2. extractionthe aqueous phase exhaustively extracted with EtOAc
  3. washthe combined organic phases washed with water again
  4. dry with materialdried over MgSO4
  5. customis purified by chromatography (silica gel, EtOAc/MeOH/NH3 90:10:1)

Sources & evidence

ORD record
ord-19782b2cbdd64e88ae81b62b2de4fba3
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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