Dimethylformamide → 4-chloro-1-(4-chlorobenzyl)-1H-pyrrole-2-carboxylic acid

HRID 1909865Notes

Reaction equation

HRID 1909865 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:7]([OH:9])=[O:8])[NH:5][CH:6]=1.CN(C=O)C.CC(C)([O-])C.[K+].Br[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1>O>[Cl:1][C:2]1[CH:3]=[C:4]([C:7]([OH:9])=[O:8])[N:5]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 71308424-chloro-1H-pyrrole-2-carboxylic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 583067404-chloro-1-(4-chlorobenzyl)-1H-pyrrole-2-carboxylic acidYield 16.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-chloro-1H-pyrrole-2-carboxylic acid (0.20 g) and DMF (2.0 mL) was added potassium tert-butoxide (0.31 g) under ice-cooling, followed by stirring at room temperature for 15 minutes. To the reaction mixture was added 1-bromomethyl-4-chlorobenzene (0.29 g) under ice-cooling, followed by stirring at room temperature for 14 hours. To the reaction mixture was added water at room temperature, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 4-chloro-1-(4-chlorobenzyl)-1H-pyrrole-2-carboxylic acid (0.06 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringby stirring at room temperature for 14 hours
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-194a3d9a5d4b43d8bccaa468bfcf5b10
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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