9-Benzyl-3-formylcarbazole → Carbazole-3-carboxaldehyde
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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