Sodium Cyanide → (3-Acetyl-5-bromo-4-hydroxy-phenyl)-acetonitrile

HRID 983800Notes

Reaction equation

HRID 983800 reaction equation
[Br:1][C:2]1[C:3]([OH:13])=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([CH2:8]Cl)[CH:7]=1.[C-:14]#[N:15].[Na+]>CS(C)=O.O>[C:10]([C:4]1[CH:5]=[C:6]([CH2:8][C:14]#[N:15])[CH:7]=[C:2]([Br:1])[C:3]=1[OH:13])(=[O:12])[CH3:11]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 22556911HCID 22556911, compound

Product 1

HCID 22556946(3-Acetyl-5-bromo-4-hydroxy-phenyl)-acetonitrileYield 58%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

A solution of 1-(3-Bromo-5-chloromethyl-2-hydroxy-phenyl)-ethanone 212 (7.6 mmol) in 6 mL DMSO is added dropwise to a suspension of 8.2 mmol of NaCN in 4 mL DMSO. The mixture is stirred for 12-18 h and diluted with 80 mL water to yield a solid. The solid is isolated and recrystallized from ethanol to yield (3-acetyl-5-bromo-4-hydroxy-phenyl)-acetonitrile 213 in a 58% yield.

Workup

  1. customto yield a solid
  2. customThe solid is isolated
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-3c4f98f46bc5425c9daa6d10885598ea
Source dataset
uspto-grants-2005_03
Patent number
US06867200B1

Reaction notes

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