Sodium Cyanide → (5-Bromo-2-naphthalenyl)acetonitrile

HRID 330257Notes

Reaction equation

HRID 330257 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:12]Br)=[CH:7]2.[C-:14]#[N:15].[Na+]>CC#N.O>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:12][C:14]#[N:15])=[CH:7]2

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 113240321-Bromo-6-(bromomethyl)naphthalene

Product 1

HCID 19869673(5-Bromo-2-naphthalenyl)acetonitrileYield 99.1%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

A suspension of 5-bromo-2-bromomethylnaphthalene (4.50 g, 15 mmol) and NaCN (784 mg, 16 mmol) in 9:1 CH3CN/H2O (150 mL) was heated to reflux for 1 hour during which time the reaction mixture became homogeneous. The solution was cooled to room temperature and the volatiles removed in vacuo. The aqueous residue was partitioned between H2O (200 mL) and CH2Cl2 (200 mL). The aqueous phase was further washed with CH2Cl2 (1×200 mL) and the combined organic layers dried (Na2SO4) and concentrated in vacuo to give the product as a white solid (3.66 g, 99%). This material was of sufficient purity to be used as such without purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour during which time the reaction mixture
  3. customthe volatiles removed in vacuo
  4. customThe aqueous residue was partitioned between H2O (200 mL) and CH2Cl2 (200 mL)
  5. washThe aqueous phase was further washed with CH2Cl2 (1×200 mL)
  6. dry with materialthe combined organic layers dried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c31b33663eb7486197f1f27d5a9411b6
Source dataset
uspto-grants-1990_01
Patent number
US04895861

Reaction notes

Loading…