Ethyl Bromide → 9-Ethyl-9H-carbazole-2-carbaldehyde
Reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[CH:14]=[O:15].C([O-])([O-])=O.[K+].[K+].Br[CH2:23][CH3:24].CC(=O)OCC>CN(C=O)C>[CH2:23]([N:12]1[C:13]2[CH:1]=[C:2]([CH:14]=[O:15])[CH:3]=[CH:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH3:24]Participants
Procedure
A 100-mL round-bottom flask was charged with a solution of 9H-carbazole-2-carbaldehyde (3.7 g, 18.97 mmol, 1.00 equiv) in DMF (50 mL). To this was added K2CO3 (5.23 g, 37.90 mmol, 2.00 equiv) followed by addition of bromoethane (10 g, 91.74 mmol, 4.80 equiv). The resulting solution was stirred overnight at room temperature. The reaction progress was monitored by TLC (EA:PE=1:3). Upon completion, the reaction mixture was quenched with water (100 mL). The resulting mixture was extracted with ethyl acetate (3×100 mL), combined organic layers were dried over sodium sulfate and concentrated on a rotary evaporator. The residue was purified by silica gel column chromatography eluted with ethyl acetate/petroleum ether (1:10) affording 9-ethyl-9H-carbazole-2-carbaldehyde as yellow solid (2.6 g, 61%).
Workup
- customUpon completion, the reaction mixture was quenched with water (100 mL)
- extractionThe resulting mixture was extracted with ethyl acetate (3×100 mL)
- dry with materialwere dried over sodium sulfate
- concentrationconcentrated on a rotary evaporator
- customThe residue was purified by silica gel column chromatography
- washeluted with ethyl acetate/petroleum ether (1:10)
Sources & evidence
- ORD record
- ord-ddc306f74e5043d5bdfdb78efb8e0900
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08080566B1
Reaction notes
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