Sodium Cyanide → (3-Acetyl-5-bromo-4-hydroxy-phenyl)-acetonitrile
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
Product 1
Reagents, catalysts & solvents 2
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
- customto yield a solid
- customThe solid is isolated
- customrecrystallized from ethanol
Sources & evidence
- ORD record
- ord-3c4f98f46bc5425c9daa6d10885598ea
- Source dataset
- uspto-grants-2005_03
- Patent number
- US06867200B1
Reaction notes
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