Water → 2-[4-Bromo-2-(trifluoromethyl)phenyl]acetonitrile

HRID 406349Notes

Reaction equation

HRID 406349 reaction equation
[C-:1]#[N:2].[K+].[Br:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11]Br)=[C:7]([C:13]([F:16])([F:15])[F:14])[CH:6]=1.O.C(OCC)(=O)C>C(O)C>[Br:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:1]#[N:2])=[C:7]([C:13]([F:16])([F:15])[F:14])[CH:6]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 8857Ethyl AcetateHCID 9032Potassium CyanideHCID 534180314-Bromo-1-(bromomethyl)-2-(trifluoromethyl)benzene

Product 1

HCID 584884072-[4-Bromo-2-(trifluoromethyl)phenyl]acetonitrileYield 89.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Potassium cyanide (630 mg) was added to an emulsion of 4-bromo-1-bromomethyl-2-trifluoromethylbenzene (3.86 g) in ethanol (15 mL)-water (5 mL), and the mixture was stirred at 70° C. for three hours and 15 minutes. Water and ethyl acetate 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=9:1) to obtain 2.28 g of the title compound. The property values of the compound are as follows.

Workup

  1. customthe organic layer was separated
  2. washThe resulting organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (carrier: Wakogel C-200; elution solvent:heptane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-3e978efbfd7341afb78fbe6d68de7d02
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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