Toluene → HCID 131729270, compound

HRID 556132Notes

Reaction equation

HRID 556132 reaction equation
C1(C)C=CC=CC=1.Br[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1.[CH2:17]([CH:20]([CH2:47][CH:48]=[CH2:49])[CH2:21][O:22][SiH2:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([SiH2:37][O:38][CH2:39][CH:40]([CH2:44][CH:45]=[CH2:46])[CH2:41][CH:42]=[CH2:43])=[CH:33][CH:32]=2)=[CH:26][CH:25]=1)[CH:18]=[CH2:19].CC([O-])(C)C.[Na+]>CCOCC.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]>[CH2:44]([CH:40]([CH2:41][CH:42]=[CH2:43])[CH2:39][O:38][SiH2:37][C:34]1[CH:35]=[CH:36][C:31]([N:30]([C:27]2[CH:26]=[CH:25][C:24]([SiH2:23][O:22][CH2:21][CH:20]([CH2:17][CH:18]=[CH2:19])[CH2:47][CH:48]=[CH2:49])=[CH:29][CH:28]=2)[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH:32][CH:33]=1)[CH:45]=[CH2:46]

Participants

7

Reactant 4

HCID 1140TolueneHCID 77304-BromoanisoleHCID 23676156Sodium t-butoxideHCID 131729271HCID 131729271, compound

Product 1

HCID 131729270HCID 131729270, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 3283Diethyl EtherSolvent

Procedure

Firstly, dist. toluene (5 mL) and 4-bromoanisole (58 μL, 0.46 mmol) were added dropwise to a mixture of bis[4-(diallylethoxysilyl)phenyl]amine (111 mg, 0.23 mmol), Pd2(dba)3 (1 mg, 0.0011 mmol), (o-biphenyl)P(t-Bu) 2 (2 mg, 0.03 mmol) and NaOt-Bu (33 mg, 0.35 mmol). The resultant mixture was stirred under a nitrogen atmosphere at 80° C. for 24 hours to obtain a reaction mixture. Then, the reaction mixture was diluted with ether. A salt thus formed was removed through a celite filtration process, and the solvent was distilled away from an organic layer with an evaporator to obtain a crude product. The obtained crude product was separated and purified by PTLC (hexane/EtOAc/acetone=20/2/1) to obtain N,N-bis(4-(diallylethoxysilyl)phenyl)-4-methoxyaniline (65.8 mg, 48% yield).

Workup

  1. customto obtain a reaction mixture
  2. customA salt thus formed
  3. customwas removed through a celite filtration process
  4. distillationthe solvent was distilled away from an organic layer with an evaporator
  5. customto obtain a crude product
  6. customThe obtained crude product
  7. customwas separated
  8. custompurified by PTLC (hexane/EtOAc/acetone=20/2/1)

Sources & evidence

ORD record
ord-93e01778fda34d9a815ba4d9f850f7cb
Source dataset
uspto-grants-2011_11
Patent number
US08053588B2

Reaction notes

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