Hydrochloric Acid → 3-Chloro-5-methoxybenzonitrile

HRID 1874774Notes

Reaction equation

HRID 1874774 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8](Cl)[CH:9]=1)[C:5]#[N:6].[CH3:11][O-:12].[Na+].Cl>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:12][CH3:11])[CH:9]=1)[C:5]#[N:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 810523,5-DichlorobenzonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 219499213-Chloro-5-methoxybenzonitrileYield 90.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

3,5-Dichlorobenzonitrile (52.93 g, 307.7 mmol) was dissolved in anhydrous DMF (300 mL) and cooled to 0° C. in an ice bath. Sodium methoxide (18.28 g, 338.5 mmol) was added as a solid and the mixture was allowed to warm to RT and stirred overnight. The reaction mixture was poured into a mixture of 10% HCl and ice. The solid that formed was filtered, washed with water, and dried overnight. The solid was dissolved in EtOAc and DCM and filtered to remove insoluble material. The solution was washed with water, dried over MgSO4, filtered and evaporated to afford the title compound (46.48 g, 90%) as a solid. 1H NMR (400 MHz, CDCl3): δ ppm 7.20 (t, 1H), 7.10 (t, 1H), 7.03 (dd, 1H), 3.82 (s, 3H).

Workup

  1. temperatureto warm to RT
  2. customThe solid that formed
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried overnight
  6. dissolutionThe solid was dissolved in EtOAc
  7. filtrationDCM and filtered
  8. customto remove insoluble material
  9. washThe solution was washed with water
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-24942e008d8c4f2493de59e8b88c8e6b
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

Loading…