Potassium Cyanide → 2-(1-bromonaphthalen-2-yl)acetonitrile

HRID 1855972Notes

Reaction equation

HRID 1855972 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:12]Br.[C-:14]#[N:15].[K+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl.O>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:12][C:14]#[N:15]

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 378281-Bromo-2-(bromomethyl)naphthalene

Product 1

HCID 2343772-(1-bromonaphthalen-2-yl)acetonitrile

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 99 parts of 1-bromo-2-(bromomethyl)naphthalene, 103 parts of potassium cyanide and 1 part of benzyl triethylammonium chloride in 150 parts by volume of methylene chloride and 30 parts by volume of water is stirred at room temperature for about 72 hours. The mixture is then diluted with additional quantities of methylene chloride and water, the organic layer separated, dried over calcium sulfate, and concentrated to give α-(1-bromo-2-naphthyl)acetonitrile, as a solid.

Workup

  1. customthe organic layer separated
  2. dry with materialdried over calcium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3bf92dfc906f4dae8a086f25c09d43de
Source dataset
uspto-grants-1980_08
Patent number
US04217306

Reaction notes

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