Allyl bromide → HCID 22153237, compound

HRID 1111068Notes

Reaction equation

HRID 1111068 reaction equation
[OH-].[Na+].[F:3][C:4]([F:25])([F:24])[C:5]1[CH:6]=[C:7]([C:11]2[C:12](=[O:23])[CH:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:14][C:15]=2[NH2:16])[CH:8]=[CH:9][CH:10]=1.[CH2:26](Br)[CH:27]=[CH2:28]>O.C(Cl)Cl.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[F:3][C:4]([F:24])([F:25])[C:5]1[CH:6]=[C:7]([C:11]2[C:12](=[O:23])[CH:13]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:14][C:15]=2[NH:16][CH2:28][CH:27]=[CH2:26])[CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 3

HCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 156724942-(3-Trifluoromethylphenyl)-3-amino-5-phenyl-2-cyclopentenone

Product 1

HCID 22153237HCID 22153237, compound

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

One gram of sodium hydroxide in 4.0 ml of water is added to a mixture of 4.0 g of 2-(3-trifluoromethylphenyl)-3-amino-5-phenyl-2-cyclopentenone in 80 ml of methylene chloride at room temperature followed by the addition of 1.46 g of allyl bromide and 0.27 g of benzyltriethylammonium chloride. The resulting two-phase mixture is stirred at room temperature until the reaction is completed. The reaction mixture is washed three times with water, dried over magnesium sulfate and concentrated in vacuo. The residue is typically purified by chromatography to yield the title compound.

Workup

  1. washThe reaction mixture is washed three times with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue is typically purified by chromatography

Sources & evidence

ORD record
ord-113db9c902404a859759cb8241f07ca4
Source dataset
uspto-grants-1990_12
Patent number
US04978386

Reaction notes

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