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ChemicalBook CAS DataBase List 1-PHENYL-1H-PYRROLE-2-CARBALDEHYDE
30186-39-1

1-PHENYL-1H-PYRROLE-2-CARBALDEHYDE synthesis

10synthesis methods
-

Yield:30186-39-1 95%

Reaction Conditions:

with sodium hydroxide;trichlorophosphate in dichloromethane;N,N-dimethyl-formamide;

Steps:

5 Synthesis of 1-Phenylpyrrole-2-carbaldehyde

Synthesis of 1-Phenylpyrrole-2-carbaldehyde POCl3 (0.70 mol, 65.3 ml) was added dropwise to 76 ml of DMF and stirred for 10 min. The temperature was lowered to 0° C. and a solution of 1-phenylpyrrole (0.70 mol, 100 g) in dichloromethane (100 ml) was added dropwise. The viscous solution was slowly warmed to 50° C. and stirred for 1 h. After cooling to room temperature, the flask was opened to the air and charged with 750 g of crushed ice. A 20 wt % solution of NaOH (885 ml) was added cautiously and the mixture was immediately heated to 90-95° C. and stirred for 10 min. The flask was placed in an ice bath and the product solidified upon cooling. The solids were collected on a filter funnel, washed with water, re-dissolved in dichloromethane, and dried over MgSO4. Evaporation of the solvent yielded 114 g of an orange oil (95% yield). 1H-NMR showed the crude product contained ca. 10% 1-phenylpyrrole-3-carbaldehyde.

References:

US6444833,2002,B1

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