4-Butylaniline → HCID 68616059, compound

HRID 2373132Notes

Reaction equation

HRID 2373132 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[CH3:17][C:18]([CH3:21])([O-])[CH3:19].[Na+].[CH2:23]([C:27]1[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=1)[CH2:24][CH2:25][CH3:26]>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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH2:17]([C:18]1[CH:21]=[CH:32][C:30]([NH:31][C:2]2[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]3[CH:15]=[CH:14][C:13]([NH:31][C:30]4[CH:29]=[CH:28][C:27]([CH2:23][CH2:24][CH2:25][CH3:26])=[CH:33][CH:32]=4)=[CH:12][CH:11]=3)=[CH:4][CH:3]=2)=[CH:29][CH:19]=1)[CH2:24][CH2:23][CH3:27]

Participants

7

Reactant 3

HCID 76944-ButylanilineHCID 7020566Trans-4,4'-dibromostilbeneHCID 23676156Sodium t-butoxide

Product 1

HCID 68616059HCID 68616059, compound

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of tris(di-benzylideneacetone)dipalladium (Pd2(dba)3) (0.335 g, 0.365 mmol) and bis-(diphenylphosphino)ferrocene (DPPF) (0.294 g, 0.530 mmol) in dry toluene (20 ml) under nitrogen atmosphere was added trans-4,4′-dibromostilbene (10) (2.0 g, 5.91 mmol) at room temperature, and the resultant mixture was stirred for 10 min, sodium tert-butoxide (2.6 g) and 4-n-butyl aniline (1.77 g, 11.83 mmol) were added to this solution and stirred at 90° C. overnight. The solid was collected, washed three times with methanol and ether, and isolated in 68.8% (1.93 g) yield as an NAM-pure product. 1H NMR (CDCl3, 500 MHz) δ ppm: 7.38 (d, J=8.0 Hz, 4H), 7.10 (d, J=8.5 Hz, 4H), 7.03 (d, J=8.0 Hz, 4H), 7.0 (d, J=8.5 Hz, 4H), 6.91 (s, 2H, ═CH), 5.77 (s, 2H, NH), 2.56 (t, J=7.7 Hz, CH2, 4H), 1.59 (m, CH2, 4H), 1.37 (m, CH2, 4H), 0.94 (t, J=7.5Hz, CH3, 6H).

Workup

  1. customThe solid was collected
  2. washwashed three times with methanol and ether
  3. customisolated in 68.8% (1.93 g)
  4. customyield as an NAM-pure product

Sources & evidence

ORD record
ord-806025c519304284a704b55dca7b89bd
Source dataset
uspto-grants-2008_12
Patent number
US07459106B2

Reaction notes

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