4-Bromobenzaldehyde → HCID 59327809, compound

HRID 1193022Notes

Reaction equation

HRID 1193022 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[F:19])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].Br[C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=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]>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([N:11]([C:21]2[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=2)[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[F:19])=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 707414-BromobenzaldehydeHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxideHCID 59327800HCID 59327800, compound

Product 1

HCID 59327809HCID 59327809, 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-butyl-N-(2,4-difluorophenyl)benzeneamine (30 m mol)), 4-bromobenzaldehyde (34 m mol)), tris(dibenzylideneaceton)dipalladium(O) (0.5 m mol)), tris-tert-butylphosphine (0.9 m mol)), and sodium-tert-butoxide (40 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, reduced pressure and distillation were performed on the resulting solution. After a silica gel column chromatography, the solvent was reduced in pressure and distilled, thereby obtaining 4-(N-(4-butylphenyl)-N-(2,4-difluorophenyl)amino)benzaldehyde liquid having 7.1 g.

Workup

  1. customAfter the reaction was terminated
  2. customthe toluene was removed from the solution
  3. extractionAfter extraction
  4. distillationdichloromethane and water, reduced pressure and distillation
  5. distillationdistilled

Sources & evidence

ORD record
ord-b0ee8c19858e4947ad7d6e370dc0c595
Source dataset
uspto-grants-2014_03
Patent number
US08680336B2

Reaction notes

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