Pyridine → 2-Chloro-4-fluoro-3-methylbenzonitrile

HRID 2046623Notes

Reaction equation

HRID 2046623 reaction equation
[Cl:1][C:2]1[C:10]([CH3:11])=[C:9]([F:12])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=O.N1C=CC=CC=1.C(Cl)(=O)C(Cl)=O.C(OCC)(=O)C.O>CN(C=O)C>[Cl:1][C:2]1[C:10]([CH3:11])=[C:9]([F:12])[CH:8]=[CH:7][C:3]=1[C:4]#[N:6]

Participants

6

Reactant 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 22728543Water ethylacetateHCID 68602527HCID 68602527, compound

Product 1

HCID 445509712-Chloro-4-fluoro-3-methylbenzonitrileYield 70.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution (50 ml) of 2-chloro-4-fluoro-3-methylbenzamide (4.69 g) and pyridine (2.97 g) in DMF was added dropwise oxalyl chloride (3.80 g) with stirring under ice-cooling at not more than 10° C. After stirring at the same temperature for 1 hr, the mixture was poured into ethyl acetate/water and partitioned. The organic layer was washed with water, aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the precipitated crystals were collected by filtration, washed with cold hexane and dried to give the title compound (3.00 g) as crystals.

Workup

  1. temperaturecooling at not more than 10° C
  2. stirringAfter stirring at the same temperature for 1 hr
  3. custompartitioned
  4. washThe organic layer was washed with water, aqueous sodium hydrogencarbonate solution and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. filtrationthe precipitated crystals were collected by filtration
  8. washwashed with cold hexane
  9. customdried

Sources & evidence

ORD record
ord-bbdbcd6333bd4054bc5918106c4dc85b
Source dataset
uspto-grants-2013_11
Patent number
US08592452B2

Reaction notes

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