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

HRID 1438279Notes

Reaction equation

HRID 1438279 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Br)=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1.[C-:14]#[N:15].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:14]#[N:15])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 534180314-Bromo-1-(bromomethyl)-2-(trifluoromethyl)benzene

Product 1

HCID 584884072-[4-Bromo-2-(trifluoromethyl)phenyl]acetonitrileYield 54.1%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 21908982Water methylene chlorideSolvent

Procedure

A mixture of 4-methyl-3-trifluorobromobenzene (33.26 g, 104.261 mmol) from step 1 above KCN (20.43 g, 313.67 mmol) and tetrabutylammonium bromide (3.37 g, 10.45 mmol) in CH2Cl2/H2O 1:1 (300 mL) was stirred at room temperature for 4 hours. The layers were separated and the organic layer washed with H2O (100 mL) 1N HCl (100 mL), brine, dried over Na2SO4 and then concentrated to a brown oil which was purified by flash column chromatography (0% to 20% EtOAc in hexanes) to give the product as a clear oil (14.9 g, 54%). 1H NMR (400 MHz, CDCl3) δ 3.91 (s, 2H), 7.57 (d, J=8.3 Hz, 1H), 7.75 (dd, J=8.3, 2 Hz, 1H), 7.84 (d, J=2 Hz, 1H).

Workup

  1. customThe layers were separated
  2. washthe organic layer washed with H2O (100 mL) 1N HCl (100 mL), brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to a brown oil which
  5. customwas purified by flash column chromatography (0% to 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4de2f28e33014a559c6ddac83e22f35a
Source dataset
uspto-grants-2009_11
Patent number
US07622605B2

Reaction notes

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