Water → (3-Bromo-2,5-dimethoxy-phenyl)-acetonitrile

HRID 1794493Notes

Reaction equation

HRID 1794493 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([CH2:10]Cl)[C:3]=1[O:12][CH3:13].[C-:14]#[N:15].[K+].O>CS(C)=O>[Br:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([CH2:10][C:14]#[N:15])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 103081541-Bromo-3-chloromethyl-2,5-dimethoxy-benzene

Product 1

HCID 10149238(3-Bromo-2,5-dimethoxy-phenyl)-acetonitrileYield 77%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 1-Bromo-3-chloromethyl-2,5-dimethoxy-benzene 53 (7.0 g, 26.4 mmol) and KCN (1.7 g, 26.4 mmol) in DMSO (50 ml) was heated to 75° C. After 2 hr, the reaction was cooled and poured into water. The aqueous layer was extracted with EtOAc and the organic layer was dried and concentrated. The product was purified by column chromatography on silica gel (20% EtOac/Hex) to give 54 as an oil (5.2 g, 77%): 1H NMR (DMSO-d6) δ 7.20 (d, 1 H, J=3.0 Hz), 6.99 (d, 1 H, J=3.0 Hz), 4.00 (s, 2 H), 3.75 (s, 6 H)

Workup

  1. temperaturethe reaction was cooled
  2. extractionThe aqueous layer was extracted with EtOAc
  3. customthe organic layer was dried
  4. concentrationconcentrated
  5. customThe product was purified by column chromatography on silica gel (20% EtOac/Hex)

Sources & evidence

ORD record
ord-84fb0e07d5124db592d3d493673caede
Source dataset
uspto-grants-2006_04
Patent number
US07022733B2

Reaction notes

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