Toluene → 4-Methyl-N-(4-methylphenyl)-N-{4-[2-(4-methylphenyl)ethenyl]phenyl}aniline

HRID 1178865Notes

Reaction equation

HRID 1178865 reaction equation
O([C:3](C)(C)[CH3:4])[Na].[NH2:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[CH2:13])=[CH:10][CH:9]=1.Br[C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1.[C:24]1([CH3:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CCOC(C)=O.[CH3:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]>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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:12]([C:11]1[CH:14]=[CH:15][C:8]([N:7]([C:27]2[CH:28]=[CH:29][C:24]([CH3:30])=[CH:25][CH:26]=2)[C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)=[CH:9][CH:10]=1)=[CH2:13].[CH3:30][C:24]1[CH:29]=[CH:28][C:27]([N:7]([C:8]2[CH:9]=[CH:10][C:11]([CH3:12])=[CH:14][CH:15]=2)[C:39]2[CH:38]=[CH:37][C:42]([CH:3]=[CH:4][C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)=[CH:41][CH:40]=2)=[CH:26][CH:25]=1

Participants

8

Reactant 5

HCID 1140TolueneHCID 78054-BromotolueneHCID 737004-AminostyreneHCID 21226206Ethyl acetate hexaneHCID 178418730sodium 2-methylpropan-2-olate

Product 2

HCID 10870287HCID 10870287, compoundYield 11%HCID 542295924-Methyl-N-(4-methylphenyl)-N-{4-[2-(4-methylphenyl)ethenyl]phenyl}anilineYield 84%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Following the general procedure shown above, Pd2dba3 (18.3 mg, 2 mol %), NaO-t-Bu (336 mg, 3.5 mmol), P(isoBuNCH2CH2)3N (13.6 mg, 4 mol %), 4-aminostyrene (119 mg, 1 mmol), 4-bromotoluene (547 mg, 3.2 mmol), and 10 mL of dry toluene at 110° C. for 16 h produced (4) 4-ethenyl-N,N-bis(4-methylphenyl)benzenamine (32 mg, 11%) as a viscous liquid and (5) N,N-bis(4-methylphenyl)-4-[2-(4-methylphenyl)ethenyl]benzenamine (325 mg, 84%) as a yellow solid after chromatography with 1% EtOAc/hexane mixture. Total yield=95%. (See Entry 1 of Table 2).

Workup

  1. customat 110° C.
  2. customfor 16 h

Sources & evidence

ORD record
ord-6a47b82b54b746fd9bd69d93b59116d2
Source dataset
uspto-grants-2007_10
Patent number
US07276627B2

Reaction notes

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