4-Bromobenzaldehyde → HCID 59327794, compound

HRID 1193024Notes

Reaction equation

HRID 1193024 reaction equation
[CH3:1][Si:2]([CH3:17])([CH3:16])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.Br[C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.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]>[CH3:1][Si:2]([CH3:17])([CH3:16])[C:3]1[CH:4]=[CH:5][C:6]([N:9]([C:19]2[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 707414-BromobenzaldehydeHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxideHCID 44138892N-Phenyl-4-(trimethylsilyl)aniline

Product 1

HCID 59327794HCID 59327794, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

4-(trimethylsilyl)-N-phenylbenzeneamine (22.8 m mol)), 4-bromobenzaldehyde (29.64 m mol)), tris(dibenzylideneaceton)dipalladium(O) (0.342 m mol)), tris-tert-butyl phosphine (0.684 m mol)), and sodium-tert-butoxide (29.64 m mol)) were dissolved in toluene (100 ml) in a 250 ml tri-neck-round bottom flask and were 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-(N-(4-(trimethylsilyl)phenyl)-N-phenylamino)benzaldehyde liquid having 4.1 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-2cfb52ab518847418a8733955291ffe3
Source dataset
uspto-grants-2014_03
Patent number
US08680336B2

Reaction notes

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