Potassium Cyanide → 3-Bromo-5-methoxyphenol

HRID 473521Notes

Reaction equation

HRID 473521 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10]C)[CH:3]=1.[C-]#N.[K+]>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([OH:10])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 6391871-Bromo-3,5-dimethoxybenzene

Product 1

HCID 215360383-Bromo-5-methoxyphenol

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

1-Bromo-3,5-dimethoxy-benzene (0.217 g, 0.001 mol) and KCN (0.20 g, 0.003 mol) were taken up into DMSO (10 mL) and the resulting mixture stirred at 120° C. for six hours, then at 150° C. overnight. The mixture was maintained at this temperature, with stirring for another day. The reaction was then quenched with water and the resulting mixture extracted with EtOAc. The organic layer was washed with saturated NaHCO3, brine, then dried over sodium sulfate and the solvent removed in vacuo. The resulting residue was purified on normal phase chromatography (Heptane/EtOAc) to yield 3-bromo-5-methoxyphenol. MH+ 203, 205

Workup

  1. customat 150° C.
  2. customovernight
  3. temperatureThe mixture was maintained at this temperature
  4. stirringwith stirring for another day
  5. customThe reaction was then quenched with water
  6. extractionthe resulting mixture extracted with EtOAc
  7. washThe organic layer was washed with saturated NaHCO3, brine
  8. dry with materialdried over sodium sulfate
  9. customthe solvent removed in vacuo
  10. customThe resulting residue was purified on normal phase chromatography (Heptane/EtOAc)

Sources & evidence

ORD record
ord-d2e1205e8cea470287f0131f02fe58df
Source dataset
uspto-grants-2014_01
Patent number
US08633322B2

Reaction notes

Loading…