Chloromethyl ethyl ether → HCID 19103176, compound

HRID 466626Notes

Reaction equation

HRID 466626 reaction equation
[Br:1][C:2]1[C:6]([C:7]([F:10])([F:9])[F:8])=[C:5]([C:11]([F:14])([F:13])[F:12])[NH:4][C:3]=1[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1.CC(C)([O-])C.[K+].[CH2:29]([O:31][CH2:32]Cl)[CH3:30]>O1CCCC1>[Br:1][C:2]1[C:6]([C:7]([F:10])([F:9])[F:8])=[C:5]([C:11]([F:14])([F:12])[F:13])[N:4]([CH2:32][O:31][CH2:29][CH3:30])[C:3]=1[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1

Participants

5

Reactant 3

HCID 18523Chloromethyl ethyl etherHCID 19103162HCID 19103162, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19103176HCID 19103176, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a chilled solution of 3-bromo-2-(3,4-dichlorophenyl)-4,5-bis(trifluoromethyl)pyrrole (0.854 g, 2 mmol) and tetrahydrofuran is added potassium tertbutoxide (0.247 g, 2.2 mmol). After stirring at ice bath temperature for 15 minutes chloromethyl ethyl ether (0.208 g, 2.2 mmol) is added to the reaction mixture and the ice bath is removed. Stirring is continued for 1 1/2 hours then the reaction mixture is diluted with water and extracted with ether. The combined organic extracts are washed sequentially with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a yellow liquid (0.91 g, 94%). Identified by IR and NMR spectral analyses.

Workup

  1. additionis added to the reaction mixture
  2. customthe ice bath is removed
  3. customis continued for 1 1/2 hours
  4. additionthe reaction mixture is diluted with water
  5. extractionextracted with ether
  6. washThe combined organic extracts are washed sequentially with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2039d49a7cd94211b15f83c5ec686801
Source dataset
uspto-grants-1992_10
Patent number
US05157047

Reaction notes

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