Water → 3-Bromo-4-ethoxybenzonitrile

HRID 1865040

Reaction equation

HRID 1865040 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[OH:16])[C:11]#[N:12].I[CH2:18][CH3:19].O>CC(C)=O>[Br:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[O:16][CH2:18][CH3:19])[C:11]#[N:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 753413-Bromo-4-hydroxybenzonitrile

Product 1

HCID 22390723-Bromo-4-ethoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Add potassium carbonate (5.2 g, 37.9 mmol) to 3-bromo-4-hydroxy-benzonitrile (5.0 g, 25.2 mmol) in acetone with stirring at room temperature. After 15 minutes, add iodoethane (2.4 mL, 130.3 mmol) and continue stirring at room temperature. After 18 hours, pour the reaction mixture into water and extract with EtOAc. Combine the organic extracts, wash with water and brine, dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. Purify the residue by flash chromatography eluting with ethyl acetate:hexanes to provide the title compound.

Workup

  1. stirringcontinue stirring at room temperature
  2. waitAfter 18 hours
  3. extractionextract with EtOAc
  4. washwash with water and brine
  5. dry with materialdry over anhydrous magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure
  8. customPurify the residue by flash chromatography
  9. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-52df170b0f6f49aab8a21edd1c1df123
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Linked notes

Loading…