Chloromethyl ethyl ether → HCID 18930413, compound

HRID 1975216Notes

Reaction equation

HRID 1975216 reaction equation
[Br:1][C:2]1[C:6]([S:7][C:8]([F:11])([F:10])[F:9])=[C:5]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[NH:4][C:3]=1[C:19]([F:22])([F:21])[F:20].CC(C)([O-])C.[K+].[CH2:29]([O:31][CH2:32]Cl)[CH3:30]>O1CCCC1.CCOCC.O>[Br:1][C:2]1[C:6]([S:7][C:8]([F:10])([F:9])[F:11])=[C:5]([C:12]2[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=2)[N:4]([CH2:32][O:31][CH2:29][CH3:30])[C:3]=1[C:19]([F:22])([F:21])[F:20]

Participants

6

Reactant 3

HCID 18523Chloromethyl ethyl etherHCID 18930383HCID 18930383, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18930413HCID 18930413, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584184Diethylether waterSolvent

Procedure

A solution of 3-bromo-5-(p-chlorophenyl)-2-(trifluoromethyl)-4-[(trifluoromethyl)thio]pyrrole (0.6 g, 1.4 mmol) and potassium tert-butoxide (0.19 g, 1.7 mmol) in tetrahydrofuran is stirred for 15 minutes, treated with chloromethyl ethyl ether (0.16 g, 1.7 mmol), stirred for 30 minutes and diluted with an ether/water mixture. The organic phase is separated, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a residue. Chromatography of the residue using silica gel and a 1:9 ethyl acetate/hexanes solution gives the title product as an amber oil which is identified by 1HNMR and 13CNMR spectral analyses.

Workup

  1. customThe organic phase is separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto obtain a residue

Sources & evidence

ORD record
ord-fec026b68e8a4afb963ff6139ac002fc
Source dataset
uspto-grants-1994_02
Patent number
US05284863

Reaction notes

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