Ethyl 1H-pyrrole-2-carboxylate → Ethyl 1-(4-chloro-2-nitrobenzyl)-pyrrole-2-carboxylate

HRID 1982388Notes

Reaction equation

HRID 1982388 reaction equation
CC(C)([O-])C.[K+].[NH:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[C:12]([O:14][CH2:15][CH3:16])=[O:13].[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[C:20]([N+:26]([O-:28])=[O:27])[CH:19]=1>CN(C)C=O>[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][N:7]2[CH:11]=[CH:10][CH:9]=[C:8]2[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:20]([N+:26]([O-:28])=[O:27])[CH:19]=1

Participants

5

Reactant 3

HCID 255670Ethyl 1H-pyrrole-2-carboxylateHCID 105868161-(Bromomethyl)-4-chloro-2-nitrobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 13649560Ethyl 1-(4-chloro-2-nitrobenzyl)-pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a solution of 493 mg of potassium tert-butoxide in 5 mL of dimethylformamide (anhydrous) is added dropwise a solution of 556 mg of ethyl pyrrole-2-carboxylate (prepared as described in Organic Synthesis, Vol. 51, p. 100) in 5 mL of anhydrous dimethylformamide. On completion of the addition the mixture is allowed to stir at room temperature for 1 hour. To this mixture is added a solution of 1 g of 4-chloro-2-nitrobenzyl bromide in 5 mL of dimethylformamide. The reaction mixture is then heated to 75° and maintained at this temperature for 18 hours, then allowed to cool to room temperature. The reaction mixture is poured into 20 mL of ice-water and extracted with 2×30 mL of ether. The combined ethereal extracts are washed with 2×30 mL of water followed by 30 mL of saturated sodium bicarbonate solution. The ethereal extracts are dried over anhydrous sodium sulfate and the solvent evaporated under reduced pressure to yield ethyl 1-(4-chloro-2-nitrobenzyl)-pyrrole-2-carboxylate melting at 104°-106°.

Workup

  1. additionOn completion of the addition the mixture
  2. temperatureThe reaction mixture is then heated to 75°
  3. temperaturemaintained at this temperature for 18 hours
  4. temperatureto cool to room temperature
  5. extractionextracted with 2×30 mL of ether
  6. washThe combined ethereal extracts are washed with 2×30 mL of water
  7. dry with materialThe ethereal extracts are dried over anhydrous sodium sulfate
  8. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-5cb0cbeac9974c62a520b3650e44abc9
Source dataset
uspto-grants-1986_06
Patent number
US04596799

Reaction notes

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