Allyl bromide → HCID 20247555, compound

HRID 1589099Notes

Reaction equation

HRID 1589099 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[C:14](=[O:15])[C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)=[C:12]([NH2:26])[O:11]1.[CH2:27](Br)[CH:28]=[CH2:29]>O.C(Cl)Cl.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[C:14](=[O:15])[C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:23])([F:24])[F:25])[CH:17]=2)=[C:12]([NH:26][CH2:29][CH:28]=[CH2:27])[O:11]1

Participants

7

Reactant 3

HCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 20247587HCID 20247587, compound

Product 1

HCID 20247555HCID 20247555, compoundYield 55.9%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

One gram of sodium hydroxide in 4.0 ml of water was added to a mixture of 4.0 g of 2-(2-fluorophenyl)-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran in 80 ml of methylene chloride at room temperature followed by the addition of 1.44 g of allyl bromide and 0.27 g of benzyltriethylammonium chloride. The resulting two-phase mixture was stirred at room temperature for about 18 hours after which time it was washed three times with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by chromatography over silica gel eluting with chloroform to yield 2.5 g of the title compound.

Workup

  1. washwas washed three times with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography over silica gel eluting with chloroform

Sources & evidence

ORD record
ord-fc7e5ae32237402ca35b8da268a0df00
Source dataset
uspto-grants-1986_02
Patent number
US04568376

Reaction notes

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