Sodium Cyanide → HCID 18451536, compound

HRID 1270795Notes

Reaction equation

HRID 1270795 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[CH:5][C:6]([I:11])=[C:7]([CH:10]=1)[CH2:8]Br.[C-:14]#[N:15].[Na+]>CCO.O>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[CH:5][C:6]([I:11])=[C:7]([CH2:8][C:14]#[N:15])[CH:10]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 184515342-(Bromomethyl)-1-iodo-4-(trifluoromethyl)benzene

Product 1

HCID 18451536HCID 18451536, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 5-trifluoromethyl-2-iodobenzyl bromide (55 g, 0.15 mol) in EtOH (200 mL) is stirred at room temperature and a solution of sodium cyanide (16 g, 0.33 mol) in water (60 mL) is added. The reaction mixture is heated to reflux temperature for 3 hours and then cooled to room temperature. Most of the ethanol is removed by rotary evaporator and the residue partitioned between EtOAc (500 mL) and water (200 mL). The organic layer is washed with brine (250 mL), dried (MgSO4) and the solvent is removed by rotary evaporator. The residue is purified using flash chromatography (1:9 EtOAc/hexanes) to give 5-trifluoromethyl-2-iodophenylacetonitrile as a solid.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux temperature for 3 hours
  3. customMost of the ethanol is removed by rotary evaporator
  4. customthe residue partitioned between EtOAc (500 mL) and water (200 mL)
  5. washThe organic layer is washed with brine (250 mL)
  6. dry with materialdried (MgSO4)
  7. customthe solvent is removed by rotary evaporator
  8. customThe residue is purified

Sources & evidence

ORD record
ord-512ffc7cefa94ad8a10870b78588328a
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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