HCID 14770843, compound → HCID 14770834, compound

HRID 1651575Notes

Reaction equation

HRID 1651575 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH:9]2[CH2:13][CH2:12][CH:11](Cl)[CH2:10]2)=[CH:4][C:3]=1[F:15].[C:16]1(=[O:26])[NH:20][C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12.[K]>CN(C)C=O>[Br:1][C:2]1[C:3]([F:15])=[CH:4][C:5]([CH:9]2[CH2:13][CH2:12][CH:11]([N:20]3[C:16](=[O:26])[C:17]4[C:18](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:19]3=[O:21])[CH2:10]2)=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 14770843HCID 14770843, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 14770834HCID 14770834, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 29.6 g (0.1 mol) of 1-bromo-4-(3-chlorocyclopentyl)-2,5-difluorobenzene in 150 ml of dry dimethylformamide was treated with 19.4 g (0.105 mol) of potassium phthalimide and the resulting suspension stirred at 100° for 8 hours and room temperature overnight. The solvent was removed in vacuo, and the residue was partitioned between methylene chloride and water. The aqueous layer was reextracted with methylene chloride and the combined organic layers were washed with water, dried (MgSO4), filtered, and evaporated in vacuo to give 36.8 g of the title compound as a viscous oil which crystallized on standing and had mp 44°-47°.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between methylene chloride and water
  3. washthe combined organic layers were washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-a2e82acc929d4009abc87e27df2649bf
Source dataset
uspto-grants-1990_05
Patent number
US04929613

Reaction notes

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