Pyrrole-2-carboxaldehyde → HCID 19383047, compound

HRID 2399674Notes

Reaction equation

HRID 2399674 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[O:7].[H-].[Na+].[Cl:10][C:11]1[CH:12]=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:14]=[CH:15][C:16]=1F>CN(C)C=O>[Cl:10][C:11]1[CH:12]=[C:13]([C:18]([F:19])([F:20])[F:21])[CH:14]=[CH:15][C:16]=1[N:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[O:7]

Participants

5

Reactant 3

HCID 13854Pyrrole-2-carboxaldehydeHCID 24758Sodium hydrideHCID 157153Benzene, 2-chloro-1-fluoro-4-(trifluoromethyl)-

Product 1

HCID 19383047HCID 19383047, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of pyrrole-2-carboxaldehyde (19.0 g, 0.2 mol) in N,N-dimethylformamide (50 ml) was added dropwise to a suspension of sodium hydride (80% dispersion in oil, 6.3 g, 0.21 mol) in N,N-dimethylformamide (100 ml), maintaining the temperature of the reaction between 5°-10° C. by means of ice-bath cooling. When the addition was complete, stirring was continued for 30 minutes, and then 3-chloro-4-fluorobenzotrifluoride (39.7 g, 0.20 mol) added. The mixture was stirred for 3 hours, then warmed to 50° C. for 18 hours. The mixture was cooled to room temperature and partitioned between diethyl ether and water. The ethereal extract was washed sequentially with water and brine, dried over magnesium sulfate, filtered and the filtrate evaporated. Trituration with hexane gave 1-(2'-chloro-4'-trifluoromethylphenyl)pyrrole-2-carboxaldehyde as a pale yellow solid (30.6 g), m.p. 119°-120° C.

Workup

  1. temperaturemaintaining
  2. customthe temperature of the reaction between 5°-10° C. by means of ice-bath
  3. temperaturecooling
  4. additionWhen the addition
  5. stirringThe mixture was stirred for 3 hours
  6. temperatureThe mixture was cooled to room temperature
  7. custompartitioned between diethyl ether and water
  8. extractionThe ethereal extract
  9. washwas washed sequentially with water and brine
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. customthe filtrate evaporated

Sources & evidence

ORD record
ord-a3b19aa5a29e40eb81410bfd06d0a4b3
Source dataset
uspto-grants-1995_09
Patent number
US05451566

Reaction notes

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