Chloromethyl ethyl ether → HCID 18969615, compound

HRID 399027Notes

Reaction equation

HRID 399027 reaction equation
[Br:1][C:2]1[C:6]([S:7]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)(=[O:9])=[O:8])=[C:5]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[NH:4][C:3]=1[C:24]([F:27])([F:26])[F:25].CC(C)([O-])C.[K+].[CH2:34]([O:36][CH2:37]Cl)[CH3:35]>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[C:6]([S:7]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)(=[O:8])=[O:9])=[C:5]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:4]([CH2:37][O:36][CH2:34][CH3:35])[C:3]=1[C:24]([F:25])([F:26])[F:27]

Participants

6

Reactant 3

HCID 18523Chloromethyl ethyl etherHCID 18969606HCID 18969606, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18969615HCID 18969615, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-bromo-5-(p-chlorophenyl)-4-[(p-chlorophenyl)sulfonyl]-2-(trifluoromethyl)pyrrole (0.92 g, 1.84 mmol) and potassium tert-butoxide (0.26 g, 2.21 mmol) in tetrahydrofuran is stirred at room temperature for 5 minutes, treated with a solution of chloromethyl ethyl ether (0.21 g, 2.21 mmol) in tetrahydrofuran, stirred at room temperature overnight, diluted with ethyl acetate, washed sequentially with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give the title product as a white solid (0.98 g, mp 107°-112° C.).

Workup

  1. washwashed sequentially with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f055a922afd842df9aae6e996deeefe5
Source dataset
uspto-grants-1998_10
Patent number
US05817691

Reaction notes

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