Sodium Iodide → 2,3-Dibromo-5-(p-chlorophenyl)-1-(ethoxymethyl)-4-[(trifluoromethyl)sulfonyl]pyrrole

HRID 375178Notes

Reaction equation

HRID 375178 reaction equation
CC(C)([O-])C.[K+].[Br:7][C:8]1[NH:9][C:10]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[C:11]([S:14]([C:17]([F:20])([F:19])[F:18])(=[O:16])=[O:15])[C:12]=1[Br:13].[I-].[Na+].[CH2:30]([O:32][CH2:33]Cl)[CH3:31]>O1CCCC1.CCCCCC.O>[Br:7][C:8]1[N:9]([CH2:33][O:32][CH2:30][CH3:31])[C:10]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[C:11]([S:14]([C:17]([F:20])([F:19])[F:18])(=[O:16])=[O:15])[C:12]=1[Br:13]

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 18523Chloromethyl ethyl etherHCID 152784202,3-Dibromo-5-(p-chlorophenyl)-4-[(trifluoromethyl)sulfonyl]pyrroleHCID 23665647Potassium tert-butoxide

Product 1

HCID 189304092,3-Dibromo-5-(p-chlorophenyl)-1-(ethoxymethyl)-4-[(trifluoromethyl)sulfonyl]pyrroleYield 74.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of potassium tert-butoxide (0.62 g, 0.0055 mol) in tetrahydrofuran is treated with 2,3-dibromo-5-(p-chlorophenyl)-4-[(trifluoromethyl)sulfonyl]pyrrole (2.34 g, 0.005 mol), stirred for 15 minutes, treated with sodium iodide (0.82 g, 0.0055 mol), stirred for five minutes, treated with a solution of chloromethyl ethyl ether (0.52 g, 0.0055 mol) in tetrahydrofuran, stirred at room temperature for several hours, poured into water and extracted with ether. The combined organic extracts are washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give an orange oil. The oil is slurried in hexane and filtered to obtain the title product as a pale yellow solid (1.95 g, mp 133°-135° C.) which is identified by 1HNMR and 19FNMR spectral analyses.

Workup

  1. stirringstirred for five minutes
  2. stirringstirred at room temperature for several hours
  3. extractionextracted with ether
  4. washThe combined organic extracts are washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give an orange oil
  8. filtrationfiltered

Sources & evidence

ORD record
ord-e4d00524225c4c9aacb213798e74a793
Source dataset
uspto-grants-1996_01
Patent number
US05484807

Reaction notes

Loading…