Benzene → 2-Chloro-4-fluoro-1-nitrobenzene

HRID 27316

Reaction equation

HRID 27316 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([F:8])[CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.[N+:14]([O-])([OH:16])=[O:15].C1C=CC=CC=1>CCCCCC>[Cl:1][C:2]1[CH:3]=[C:4]([F:8])[CH:5]=[CH:6][C:7]=1[N+:14]([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 241BenzeneHCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 2230871-Chloro-3-fluorobenzene

Product 1

HCID 750172-Chloro-4-fluoro-1-nitrobenzeneYield 16.7%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

m-Chlorofluorobenzene (240 g. 1.85 moles) is added to a mixture of sulfuric acid (185 g. 1.85 moles) and nitric acid (166 g., 1.85 moles) at -5° C. in 3.5 hours, stirred 13 hours, then benzene (200 ml.) and hexane (200 ml.) are added. The extract is washed with water (1×300 ml.), sodium carbonate solution (1×300 ml.), and water (1×300 ml.), dried and the solvents removed. The residue is distilled to give 138 g. of mixed isomers. The 4-nitro isomer crystallizes and is filtered off to give 3-chloro-4-nitrofluorobenzene (51 g. 16.7%) m.p. 36°-38° C.

Workup

  1. washThe extract is washed with water (1×300 ml.), sodium carbonate solution (1×300 ml.), and water (1×300 ml.)
  2. customdried
  3. customthe solvents removed
  4. distillationThe residue is distilled
  5. customto give 138 g
  6. customThe 4-nitro isomer crystallizes
  7. filtrationis filtered off

Sources & evidence

ORD record
ord-3b20832d80754f30b3a7f15ac0a9a9ff
Source dataset
uspto-grants-1980_09
Patent number
US04220468

Linked notes

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