N,N'-Dimethylethylenediamine → n-(2,4-Difluorophenyl)-n,n'-dimethylethylene-1,2-diamine

HRID 2182212Notes

Reaction equation

HRID 2182212 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[F:9].[CH3:10][NH:11][CH2:12][CH2:13][NH:14][CH3:15].O(C(C)(C)C)[Na].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[F:9][C:3]1[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=1[N:11]([CH3:10])[CH2:12][CH2:13][NH:14][CH3:15]

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 676741-Bromo-2,4-difluorobenzeneHCID 634876Binap, (A+-)-HCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 22052023n-(2,4-Difluorophenyl)-n,n'-dimethylethylene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 1140TolueneSolvent

Procedure

Combine 1-bromo-2,4-difluorobenzene (1.00 g, 5.18 mmol), N,N′-dimethylethylenediamine (2.74 g, 31.1 mmol), NaO-t-Bu (0.70 g, 7.2 mmol), Pd(dba)2 (0.060 g, 0.10 mmol) and (+)-BINAP (0.19 g, 0.31 mmol) in toluene (10 ml). Heat at 110° for 18 h, allow to cool, and extract with 1N HCl. Basify the aqueous solution with NaOH and extract with CH2Cl2. Dry, concentrate, and purify by PLC to give N-(2,4-difluorophenyl)-N,N′-dimethylethylenediamine.

Workup

  1. temperatureHeat at 110° for 18 h
  2. temperatureto cool
  3. extractionextract with 1N HCl
  4. extractionextract with CH2Cl2
  5. customDry
  6. concentrationconcentrate
  7. custompurify by PLC

Sources & evidence

ORD record
ord-842e21b030ca4906ada738bdc3649c2f
Source dataset
uspto-grants-2005_05
Patent number
US06897216B2

Reaction notes

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