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

HRID 1835996Notes

Reaction equation

HRID 1835996 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-ff088186f6264dc9a81d033c904adf55
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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