Heptane → 2-(4-Bromo-2-trifluoromethylphenyl)-5-chloropentanenitrile

HRID 406350Notes

Reaction equation

HRID 406350 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.[H-].[Na+].[Cl:17][CH2:18][CH2:19][CH2:20]I.CCCCCCC>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:20][CH2:19][CH2:18][Cl:17])[C:9]#[N:10])=[C:4]([C:11]([F:12])([F:13])[F:14])[CH:3]=1

Participants

6

Reactant 4

HCID 8900HeptaneHCID 24758Sodium hydrideHCID 813631-Chloro-3-iodopropaneHCID 584884072-[4-Bromo-2-(trifluoromethyl)phenyl]acetonitrile

Product 1

HCID 666187502-(4-Bromo-2-trifluoromethylphenyl)-5-chloropentanenitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (4-bromo-2-trifluoromethylphenyl)acetonitrile (2.28 g) in tetrahydrofuran (6 mL) was added to a suspension of sodium hydride (containing 60% in mineral oil, 362 mg) in tetrahydrofuran (12 mL) under ice-cooling. The mixture was stirred at the same temperature for 20 minutes. 1-Chloro-3-iodopropane (0.94 mL) was added dropwise to the reaction solution, and then the reaction solution was stirred at room temperature for 40 minutes. Ice water and heptane were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (carrier: Wakogel™ C-200; elution solvent:heptane:ethyl acetate=49:1→19:1) to obtain 2.67 g of the title compound. The property values of the compound are as follows.

Workup

  1. temperaturecooling
  2. stirringthe reaction solution was stirred at room temperature for 40 minutes
  3. customthe organic layer was separated
  4. washThe resulting organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (carrier: Wakogel™ C-200; elution solvent:heptane:ethyl acetate=49:1→19:1)

Sources & evidence

ORD record
ord-453ed83376d14b0b94503e9d9e995ca8
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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