9-Benzyl-3-formylcarbazole → Carbazole-3-carboxaldehyde

HRID 659615Notes

Reaction equation

HRID 659615 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].C([N:12]1[C:24]2[CH:23]=[CH:22][C:21]([CH:25]=[O:26])=[CH:20][C:19]=2[C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2)C1C=CC=CC=1>ClCCCl>[CH:23]1[C:24]2[NH:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:19]=2[CH:20]=[C:21]([CH:25]=[O:26])[CH:22]=1

Participants

4

Reactant 2

HCID 30915349-Benzyl-3-formylcarbazoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 504067Carbazole-3-carboxaldehydeYield 40%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A 250-mL round-bottomed flask was charged with a solution of AlCl3 (9.26 g, 69.45 mmol, 20.00 equiv, 99%) in 1,2-dichloroethane (150 mL). To this was added 9-benzyl-9H-carbazole-3-carbaldehyde (1 g, 3.47 mmol, 1.00 equiv, 99%) in several batches at room temperature over 5 minutes. The resulting mixture was stirred for 2 hours at room temperature. The reaction was then quenched by the addition of H2O/ice (100 mL). The solids were filtered out. The resulting solution was extracted with DCM (3×100 mL) and the combined organic layers were concentrated on a rotary evaporator to give a residue that was purified by silica gel column chromatography eluted with PE:EtOAc (10:1) to afford 9H-carbazole-3-carbaldehyde as green solid (270 mg, 40%). LCMS: [M+H]+: 196

Workup

  1. customThe reaction was then quenched by the addition of H2O/ice (100 mL)
  2. filtrationThe solids were filtered out
  3. extractionThe resulting solution was extracted with DCM (3×100 mL)
  4. concentrationthe combined organic layers were concentrated on a rotary evaporator
  5. customto give a residue that
  6. customwas purified by silica gel column chromatography
  7. washeluted with PE

Sources & evidence

ORD record
ord-2939eb6eab99484792833ba23d7aeeff
Source dataset
uspto-grants-2011_12
Patent number
US08080566B1

Reaction notes

Loading…