Dimethylformamide → 4-(Bis(4-bromophenyl)amino)benzaldehyde

HRID 1058648Notes

Reaction equation

HRID 1058648 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:16]2[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=2)[C:9]2[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.C([Li])CCC.CCCCCC.CN(C)[CH:36]=[O:37]>O1CCCC1.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([C:9]2[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=2)[C:16]2[CH:21]=[CH:20][C:19]([CH:36]=[O:37])=[CH:18][CH:17]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8058HexaneHCID 258027Tris(4-bromophenyl)amineHCID 178418339Butyllithium

Product 1

HCID 186689044-(Bis(4-bromophenyl)amino)benzaldehydeYield 44%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In an argon atmosphere, tris(4-bromophenyl)amine (964 mg, 2.00 mmol) was dissolved in tetrahydrofuran (10 mL) and cooled to −78° C. n-Butyl lithium (a 1.6 mol/L hexane solution, 1.5 mL, 2.4 mmol) and dimethylformamide (0.19 mL, 2.4 mmol) was dripped thereto at a system temperature of −60° C. or less, followed by stirring for 10 minutes. To the reaction liquid was added water and the product was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=8/1) to give 4-[bis(4-bromophenyl)amino]benzaldehyde (377 mg, 44%).

Workup

  1. customat a system temperature of −60° C. or less
  2. customTo the reaction liquid
  3. extractionthe product was extracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=8/1)

Sources & evidence

ORD record
ord-0bea26522ce445d6a5ea5d9e85a45b24
Source dataset
uspto-grants-2003_02
Patent number
US06518268B1

Reaction notes

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