Hydrochloric Acid → 3-Chloro-5-methoxybenzonitrile

HRID 602585

Reaction equation

HRID 602585 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:9]=[C:8]([O:12][CH3:11])[CH:7]=[C:4]([CH:3]=1)[C:5]#[N:6]

Participants

5

Reactant 3

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

Product 1

HCID 219499213-Chloro-5-methoxybenzonitrileYield 86.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

step 1—A 100 ml round bottom flask was charged under a stream of nitrogen with 3,5-dichlorobenzonitrile (R-3a,7.0 g, 40.69 mmol) and anhydrous DMF (75 mL). To the solution was added sodium methoxide (2.26 g, 44.76 mmol) and resulting solution was stirred further at RT for 24 h. When the reaction was complete, aqueous 10% HCl added dropwise to the reaction vessel. The crude mixture was extracted with EtOAc and sequentially washed with aqueous acid, water and brine. The EtOAc extracts were dried (Na2SO4), filtered and the solvent was removed in vacuo to afford a crude solid which was recrystallized from hexane/acetone to afford 5.9 g (86%) of 5-chloro-3-methoxy-benzonitrile.

Workup

  1. customresulting solution
  2. extractionThe crude mixture was extracted with EtOAc
  3. washsequentially washed with aqueous acid, water and brine
  4. dry with materialThe EtOAc extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customto afford a crude solid which
  8. customwas recrystallized from hexane/acetone

Sources & evidence

ORD record
ord-7f8e5d2ac95b4b8ba3b792073f11181f
Source dataset
uspto-grants-2011_03
Patent number
US07906540B2

Linked notes

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