Oxalyl chloride → 4-Chloro-3-fluoro-5-nitrobenzonitrile

HRID 1258741Notes

Reaction equation

HRID 1258741 reaction equation
C(Cl)(=O)C([Cl:4])=O.[F:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[C:15]=1O)[C:11]#[N:12]>CN(C=O)C>[Cl:4][C:15]1[C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=1[F:7]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 679577893-Fluoro-4-hydroxy-5-nitrobenzonitrile

Product 1

HCID 679578694-Chloro-3-fluoro-5-nitrobenzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-25 °C

Procedure

Oxalyl chloride (5.44 g; 42.8 mmol) was added dropwise to a solution of 3-fluoro-4-hydroxy-5-nitrobenzonitrile (3.9 g; 21 mmol) in DMF (40 mL) at −25° C. The mixture was stirred at −25° C. for 15 min and thereafter at 80° C. for 2.5 h. The mixture was slowly poured into ice, the precipitate was filtered off and the filtrate was extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was combined with the precipitate and filtered through a plug of silica gel to give the sub-title compound.

Workup

  1. waitat 80° C. for 2.5 h
  2. additionThe mixture was slowly poured into ice
  3. filtrationthe precipitate was filtered off
  4. extractionthe filtrate was extracted with EtOAc
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. filtrationfiltered through a plug of silica gel

Sources & evidence

ORD record
ord-b41695da678e4b95ab774655d8b84587
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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