Sodium Cyanide → HCID 20432299, compound

HRID 2412391Notes

Reaction equation

HRID 2412391 reaction equation
[Br:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[CH2:9]Br)=[CH:4][CH:3]=1.[C-:17]#[N:18].[Na+]>O.C(O)C>[Br:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[CH2:9][C:17]#[N:18])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 20432293HCID 20432293, compound

Product 1

HCID 20432299HCID 20432299, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

457.8 g of the crude 2-(4-bromophenoxy)benzyl bromide are added over a period of one hour to a mixture that is boiling under reflux of 171.0 g of sodium cyanide in 160 ml of water and 44 ml of ethanol; at the same time 362 ml of ethanol are added dropwise. The mixture is subsequently boiled under reflux for a further 3 hours and then diluted with 1500 ml of water. The aqueous ethanolic phase is washed with 1000 ml of diethyl ether and the ether phase is separated off, washed twice with 200 ml of water, dried over magnesium sulphate and concentrated to dryness under 11 mm Hg. The residue is crystallised from a mixture of diethyl ether and petroleum ether and yields 2-(4-bromophenoxy)phenyl acetonitrile.

Workup

  1. temperatureunder reflux for a further 3 hours
  2. washThe aqueous ethanolic phase is washed with 1000 ml of diethyl ether
  3. customthe ether phase is separated off
  4. washwashed twice with 200 ml of water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated to dryness under 11 mm Hg
  7. customThe residue is crystallised from a mixture of diethyl ether and petroleum ether

Sources & evidence

ORD record
ord-7f7bcdd7d420462e9e11b2cabae03879
Source dataset
uspto-grants-1985_01
Patent number
US04492691

Reaction notes

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