Hydrogen Peroxide → 4-Methoxy-3-phenylphenethylamine

HRID 440541Notes

Reaction equation

HRID 440541 reaction equation
Br.Br[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[CH2:6][CH2:7][NH2:8].C(=O)([O-])[O-].[Na+].[Na+].[C:20]1(OB(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.OO>C(O)C.C1(C)C=CC=CC=1>[CH3:13][O:12][C:11]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][NH2:8])=[CH:4][C:3]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 10340Sodium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 224068232-(3-Bromo-4-methoxyphenyl)ethan-1-amine hydrobromide

Product 1

HCID 224068554-Methoxy-3-phenylphenethylamine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of tetrakis triphenylphosphine palladium (7 g), 3-bromo-4-methoxyphenethylamine hydrobromide (62.2 g) and toluene (400 ml) was stirred under nitrogen with 2M aqueous sodium carbonate solution (200 ml) and then a solution of phenyl boric acid (26.8 g) in ethanol (100 ml) was added. The mixture was heated under reflux for 48 hours then cooled and treated with 30% aqueous hydrogen peroxide solution (10 ml). The mixture was stirred at ambient temperature for 1 hour. The aqueous layer was separated and extracted with ether. The ether extracts were combined with the original organic phase. Distillation yielded 4-methoxy-3-phenylphenethylamine which was used without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 48 hours
  3. temperaturethen cooled
  4. customThe aqueous layer was separated
  5. extractionextracted with ether
  6. distillationDistillation

Sources & evidence

ORD record
ord-c173b890f7c14b75bdfa64d4eadcdfd0
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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