2-(Dimethylamino)ethanol → 2-(3-bromo-5-nitrophenoxy)-N,N-dimethylethanamine

HRID 2206362

Reaction equation

HRID 2206362 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([N+]([O-])=O)[CH:3]=1.[CH3:14][N:15]([CH3:19])[CH2:16][CH2:17][OH:18].[OH-].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1)[O:18][CH2:17][CH2:16][N:15]([CH3:19])[CH3:14]

Participants

6

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 14797Potassium HydroxideHCID 445341-Bromo-3,5-dinitrobenzene

Product 1

HCID 593139932-(3-bromo-5-nitrophenoxy)-N,N-dimethylethanamineYield 57.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

1-Bromo-3,5-dinitrobenzene (1 g, 4.1 mmol), 2-(dimethylamino)ethanol (0.54 g, 6.1 mmol), potassium hydroxide (0.45 g, 8.1 mmol), and water (0.5 mL) in DMF (5 mL) were heated at 80° C. After 20 hours, the reaction mixture was diluted with cold water and extracted with dichloromethane (2×100 mL). The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography (stepwise gradient, 2% ethyl acetate in hexanes to ethyl acetate) to give 2-(3-bromo-5-nitrophenoxy)-N,N-dimethylethanamine (669 mg, 57.2% yield) as a brown oil. HPLC: Rt=1.04 min. (PHENOMENEX® Luna 5 micron C18 4.6×30 mm, 10-90% aqueous methanol containing 0.1% TFA, 2 min. gradient, flow rate=5 mL/min., detection at 254 nm). MS (ES): m/z=290.93 [M+H]+.

Workup

  1. extractionextracted with dichloromethane (2×100 mL)
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel chromatography (stepwise gradient, 2% ethyl acetate in hexanes to ethyl acetate)

Sources & evidence

ORD record
ord-ef9a9b6f39914e55a30293fae4e90ee4
Source dataset
uspto-grants-2016_06
Patent number
US09371328B2

Linked notes

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