(2-Azido-1,1-difluoroethyl)benzene → 2,2-Difluoro-2-phenylethylamine

HRID 911571Notes

Reaction equation

HRID 911571 reaction equation
[N:1]([CH2:4][C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([F:7])[F:6])=[N+]=[N-]>CCOC(C)=O.[Pd]>[F:6][C:5]([F:7])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:4][NH2:1]

Participants

4

Reactant 1

HCID 57656188(2-Azido-1,1-difluoroethyl)benzene

Product 1

HCID 126355292,2-Difluoro-2-phenylethylamineYield 98.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve (2-azido-1,1-difluoro-ethyl)-benzene (475 mg, 2.59 mmol) in EtOAc (30 mL). Add 10% Pd/C and submit the mixture to hydrogenation under atmospheric pressure (balloon) for 1 h. Filter the catalyst through Celite® and concentrate the filtrate in vacuo to provide the title compound as an oil (400 mg, 98%) that was used without any further purification.

Workup

  1. customfor 1 h
  2. filtrationFilter the catalyst through Celite®
  3. concentrationconcentrate the filtrate in vacuo

Sources & evidence

ORD record
ord-f178a31c1b314fef81337af121289a79
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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