Water → HCID 45257781, compound

HRID 1873461Notes

Reaction equation

HRID 1873461 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:13][C:12]([C:18]3[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=3)([C:14]([F:17])([F:16])[F:15])[CH:11]=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8].CC([O-])(C)C.[K+].O>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:13][C:12]([C:18]3[CH:19]=[C:20]([Cl:25])[CH:21]=[C:22]([Cl:24])[CH:23]=3)([C:14]([F:17])([F:16])[F:15])[CH2:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 58092082HCID 58092082, compound

Product 1

HCID 45257781HCID 45257781, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3-bromo-4-fluorophenyl)-4-(3,5-dichlorophenyl)-4-(trifluoromethyl)-3,4-dihydro-2H-pyrrole (0.88 g) in THF (13 ml), t-BuOK (0.24 g) was added under ice cooling. The mixture was returned to room temperature and stirred for 16 hours. Water was added to the reaction mixture, and the aqueous layer was separated and extracted with ethyl acetate. The combined organic layers, were washed with saturated brine, and dried over magnesium sulfate. After filtering the reaction mixture, the solvent was distilled off under reduced pressure, and the resulting mixture was purified by silica gel chromatography, to obtain 5-(3-bromo-4-fluorophenyl)-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrole (0.88 g) at a yield of 100%.

Workup

  1. customwas returned to room temperature
  2. customthe aqueous layer was separated
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers, were washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationAfter filtering the reaction mixture
  7. distillationthe solvent was distilled off under reduced pressure
  8. customthe resulting mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b8135bc4e5c648b99f41eefab65b3e71
Source dataset
uspto-grants-2012_11
Patent number
US08304371B2

Reaction notes

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