Bromide ion → 2-(2-Bromo-5-methoxyphenyl)acetonitrile

HRID 1270784Notes

Reaction equation

HRID 1270784 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([Br:11])=[C:7]([CH:10]=1)[CH2:8]Br.[C-:12]#[N:13].[Na+].[Br-]>CCO.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([Br:11])=[C:7]([CH2:8][C:12]#[N:13])[CH:10]=1

Participants

6

Reactant 3

HCID 259Bromide ionHCID 8929Sodium CyanideHCID 35259512-Bromo-5-methoxybenzyl bromide

Product 1

HCID 6396662-(2-Bromo-5-methoxyphenyl)acetonitrileYield 90.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

5-Methoxy-2-bromobenzyl bromide (72.8 g, 0.26 mol) is dissolved in EtOH (280 mL) and stirred at room temperature. Sodium cyanide (38.2 g, 0.78 mol) is dissolved in water and added to the solution of the bromide. 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. A solid forms which is isolated by filtration and washed with water (500 mL). The crude material is purified using flash chromatography (CH2Cl2/hexanes, 1:1) to give 5-methoxy-2-bromophenylacetonitrile (53 g).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux temperature for 3 hours
  3. temperaturecooled to room temperature
  4. customMost of the ethanol is removed by rotary evaporator
  5. customA solid forms which is isolated by filtration
  6. washwashed with water (500 mL)
  7. customThe crude material is purified

Sources & evidence

ORD record
ord-11b3fdd9256848d8bd1a8e0aa9424de0
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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