2-(4'-Bromo-3',5'-difluorophenyl)-5-pentyl-1,3-dioxane → HCID 178444587, compound

HRID 1707525Notes

Reaction equation

HRID 1707525 reaction equation
Br[C:2]1[C:7]([F:8])=[CH:6][C:5]([CH:9]2[O:14][CH2:13][CH:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:11][O:10]2)=[CH:4][C:3]=1[F:20].[C:21]([Cu])#[N:22]>CN1C(=O)CCC1>[C:21]([C:2]1[C:7]([F:8])=[CH:6][C:5]([C@H:9]2[O:14][CH2:13][C@H:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:11][O:10]2)=[CH:4][C:3]=1[F:20])#[N:22]

Participants

4

Reactant 2

HCID 189615282-(4'-Bromo-3',5'-difluorophenyl)-5-pentyl-1,3-dioxaneHCID 178418546HCID 178418546, compound

Product 1

HCID 178444587HCID 178444587, compoundYield 153.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

9.1 g (0.026 mol) of 2-(4'-bromo-3',5'-difluorophenyl)-5-pentyl-1,3-dioxane, 3.5 g (0.0039 mol) of CuCN and 78 cm3 of NMP were refluxed for 2 hours on a mantle heater. The reactant was cooled to room temperature, and after adding 10 cm3 of EDA, it was poured in ice water, extracted with hexane and washed with an aqueous EDA solution and water. The hexane was removed, the residue was treated in a silica gel column with chloroform as solvent, and the chloroform was removed. The residue was recrystallized from a mixture of methanol and water to obtain 1.7 g (0.006mol) of trans-2-(4'-cyano-3',5'-difluorophenyl)-5-pentyl-1,3-dioxane. The phase transition temperature of this compound as measured using DSC was as follows. ##STR16## (where, C indicates crystal, and I shows isotropic liquid).

Workup

  1. additionafter adding 10 cm3 of EDA, it
  2. extractionextracted with hexane
  3. washwashed with an aqueous EDA solution and water
  4. customThe hexane was removed
  5. additionthe residue was treated in a silica gel column with chloroform as solvent
  6. customthe chloroform was removed
  7. customThe residue was recrystallized from a mixture of methanol and water

Sources & evidence

ORD record
ord-4fd12524d7f245bc897bd100a60b3188
Source dataset
uspto-grants-1994_10
Patent number
US05354502

Reaction notes

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