2,4-Difluoroaniline → HCID 59327800, compound

HRID 1193021Notes

Reaction equation

HRID 1193021 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH2:4].Br[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH3:20])=[CH:13][CH:12]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:17]([C:14]1[CH:15]=[CH:16][C:11]([NH:4][C:3]2[CH:5]=[CH:6][C:7]([F:9])=[CH:8][C:2]=2[F:1])=[CH:12][CH:13]=1)[CH2:18][CH2:19][CH3:20]

Participants

7

Reactant 4

HCID 97092,4-DifluoroanilineHCID 5210591-Bromo-4-butylbenzeneHCID 634876Binap, (A+-)-HCID 23665647Potassium tert-butoxide

Product 1

HCID 59327800HCID 59327800, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

2,4-difluoroaniline (44 m mol)), 1-bromo-4-butylbenzene (30 m mol)), palladium(II)acetate (0.4 m mol)), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.9 m mol)), and potassium-tert-butoxide (44 m mol)) were dissolved in toluene (100 ml) in a 250 ml tri-neck-round bottom flask and then stirred in a bath of 100° C. for 24 hours. After the reaction was terminated, the toluene was removed from the solution. After extraction was performed on the solution using dichloromethane and water, the resulting solution was reduced in pressure and distilled. After a silica gel column chromatography, the solvent was reduced in pressure and distilled, thereby obtaining 4-butyl-N-(2,4-difluorophenyl)benzeneamine liquid having 0.3 g.

Workup

  1. customAfter the reaction was terminated
  2. customthe toluene was removed from the solution
  3. extractionAfter extraction
  4. distillationdistilled
  5. distillationdistilled

Sources & evidence

ORD record
ord-e2d3bf22ee764bce8fd4171bf02abd16
Source dataset
uspto-grants-2014_03
Patent number
US08680336B2

Reaction notes

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