Dimethyl Sulfoxide → HCID 70362084, compound

HRID 1165416Notes

Reaction equation

HRID 1165416 reaction equation
[Br:1][C:2]1[C:3](CBr)=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[C-:14]#[N:15].[Na+].[CH3:17]S(C)=O>>[Br:1][C:2]1[CH:3]=[C:4]([CH2:17][C:14]#[N:15])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

4

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 19861650HCID 19861650, compound

Product 1

HCID 70362084HCID 70362084, compound

Procedure

A suspension of 3-bromo-2-bromomethylnaphthalene (6.0 g, 0.020 mol), DMSO (150 mL) and sodium cyanide (1.0 g, 0.020 mol) was stirred for 2 hours at room temperature. The resulting solution was added to ice/H2O and extracted well with ethyl acetate. The organic phase was dried over MgSO4, concentrated and dried in vacuo for 16 hours. Treatment of the resulting solid with diethyl ether/hexane afforded 3-bromo-2-naphthalenylacetonitrile (3.6 g), m.p. 116°-117° C.

Workup

  1. extractionextracted well with ethyl acetate
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated
  4. customdried in vacuo for 16 hours

Sources & evidence

ORD record
ord-6a0149b2203e42e784e35051402cb74e
Source dataset
uspto-grants-1990_03
Patent number
US04910019

Reaction notes

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