Sulfuric Acid → 5-Fluoro-2-nitrobenzonitrile

HRID 65329

Reaction equation

HRID 65329 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].S(=O)(=O)(O)O.[N+:15]([O-])([O-:17])=[O:16].[K+]>>[C:5]([C:4]1[CH:3]=[C:2]([F:1])[CH:9]=[CH:8][C:7]=1[N+:15]([O-:17])=[O:16])#[N:6]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 24434Potassium NitrateHCID 678803-Fluorobenzonitrile

Product 1

HCID 37564675-Fluoro-2-nitrobenzonitrileYield 86.5%

Conditions

Temperature
25 °C

Procedure

m-Fluorobenzonitrile (96.8 g., 0.8 mole) is added in two and one-half hours to a mixture of concentrated sulfuric acid (600 ml.) and potassium nitrate (80.9 g., 0.8 mole) at 3°-6° C., then allowed to warm to 25° C. The mixture is poured over cracked ice (3000 ml.), extracted with chloroform (5×250 ml.), dried and the solvent removed. The residue is extracted with pentane and dried to give 3-cyano-4-nitrofluorobenzene (115 g., 86.5%) m.p. 102°-104° C.

Workup

  1. extractionextracted with chloroform (5×250 ml.)
  2. customdried
  3. customthe solvent removed
  4. extractionThe residue is extracted with pentane
  5. customdried

Sources & evidence

ORD record
ord-8200ac9a36da4d00b9866cfd5bbd0eae
Source dataset
uspto-grants-1986_09
Patent number
US04613360

Linked notes

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