Dimethylformamide → 11-(Ethylhexyl)-11H-benzo[a]carbazole-5-carbaldehyde

HRID 2172361Notes

Reaction equation

HRID 2172361 reaction equation
[CH:1]1[C:6]2=[C:7]3[C:15](=[CH:16][CH:17]=[C:5]2[CH:4]=[CH:3][CH:2]=1)[C:14]1[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=1)[NH:8]3.CN([CH:21]=[O:22])C.P(Cl)(Cl)(Cl)=O>>[CH2:6]([CH:1]([N:8]1[C:7]2[C:6]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[C:17]([CH:21]=[O:22])=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:17])[CH3:7]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 9196Benzo[a]carbazoleHCID 24813Phosphorus oxychloride

Product 1

HCID 8669052711-(Ethylhexyl)-11H-benzo[a]carbazole-5-carbaldehydeYield 87.7%

Conditions

Temperature
130 °C

Procedure

To 11H-benzo[a]carbazole (3.00 g, 9.12 mmol) in DMF (7.02 g, 96.1 mmol) is added phosphoryl chloride (14.0 g, 91.3 mmol) at 0° C. After stirring for 2 hours, the mixture is heated at 130° C., and it is stirred for 1 hour. The mixture is cooled at room temperature, and poured into ice-water. The crude product is extracted with CH2Cl2, and it is washed with water and brine. The organic layer is dried over MgSO4. After concentration, the crude product is purified by column chromatography on silica gel eluting with CH2Cl2 to obtain an off-white solid (1.43 g, 43%). The structure is confirmed by 1H-NMR spectrum (CDCl3). δ [ppm]: 0.80-0.90 (m), 1.21-1.46 (m), 2.25 (m), 4.68 (m), 7.40 (t), 7.52-7.60 (m), 7.66-7.74 (m), 8.19 (s), 8.61 (d), 8.64 (s), 9.65 (d), 10.39 (s).

Workup

  1. stirringit is stirred for 1 hour
  2. temperatureThe mixture is cooled at room temperature
  3. extractionThe crude product is extracted with CH2Cl2, and it
  4. washis washed with water and brine
  5. dry with materialThe organic layer is dried over MgSO4
  6. concentrationAfter concentration
  7. customthe crude product is purified by column chromatography on silica gel eluting with CH2Cl2

Sources & evidence

ORD record
ord-2c5f8d54ebaf472c8366d7a4ab26c82a
Source dataset
uspto-grants-2015_06
Patent number
US09051397B2

Reaction notes

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