Hydrochloric Acid → 3-Bromo-2,4-dichloro-5-fluoronitrobenzene

HRID 1761644Notes

Reaction equation

HRID 1761644 reaction equation
[Br:1][C:2]1[C:8]([Cl:9])=[C:7]([F:10])[CH:6]=[C:5]([N+:11]([O-:13])=[O:12])[C:3]=1N.C(ON=O)(C)(C)C.[ClH:21]>C(#N)C>[Br:1][C:2]1[C:3]([Cl:21])=[C:5]([N+:11]([O-:13])=[O:12])[CH:6]=[C:7]([F:10])[C:8]=1[Cl:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 137487952-Bromo-3-chloro-4-fluoro-6-nitrobenzenamine

Product 1

HCID 137487963-Bromo-2,4-dichloro-5-fluoronitrobenzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of anhydrous cupric chloride (147 g) and 2-bromo-3-chloro-4-fluoro-6-nitroaniline (235.6 g) in anhydrous acetonitrile (1.5 litter) was added tert-butylnitrite (135.2 g) at 60° C. during 70 minutes. The reaction mixture was poured into ice-chilled diluted hydrochloric acid (1.5 litter) and extracted with benzene. The organic layer was successively washed with ice-chilled diluted hydrochloric acid and water saturated with sodium chloride, dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified by distillation to give the title compound (218.8 g), bp 78°-117° C./2 mmHg. The oil was crystallized from methanol to give yellow prisms, mp 65.5°-67.5° C.

Workup

  1. additionThe reaction mixture was poured into ice-
  2. extractionextracted with benzene
  3. washThe organic layer was successively washed with ice-
  4. temperaturechilled diluted hydrochloric acid and water saturated with sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. distillationThe resulting residue was purified by distillation

Sources & evidence

ORD record
ord-5dfc557fcc044fec826692726a7e466f
Source dataset
uspto-grants-1989_05
Patent number
US04826982

Reaction notes

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