Aniline → N-Phenyl-4-(trimethylsilyl)aniline

HRID 1193023Notes

Reaction equation

HRID 1193023 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:9]1[CH:14]=[CH:13][C:12]([Si:15]([CH3:18])([CH3:17])[CH3:16])=[CH:11][CH:10]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>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]>[CH3:16][Si:15]([CH3:18])([CH3:17])[C:12]1[CH:13]=[CH:14][C:9]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 138897Silane, (4-bromophenyl)trimethyl-HCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxide

Product 1

HCID 44138892N-Phenyl-4-(trimethylsilyl)aniline

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

Aniline (127.5 m mol)), (4-bromophenyl)trimethylsilane (102 m mol)), tris(dibenzylideneaceton)dipalladium(O) (1.53 m mol)), BINAP(2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (3.06 m mol)), and sodium-tert-butoxide (132.6 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-(trimethylsilyl)-N-phenylbenzeneamine 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-c357b925f8ba4461b05f9660ef9dfb61
Source dataset
uspto-grants-2014_03
Patent number
US08680336B2

Reaction notes

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