Hydrochloric Acid → 5-Bromo-4-chloro-2-fluorotoluene

HRID 369240Notes

Reaction equation

HRID 369240 reaction equation
N(OCCCC)=O.[Br:8][C:9]1[CH:15]=[C:14]([CH3:16])[C:13]([F:17])=[CH:12][C:10]=1N.[ClH:18]>C(#N)C>[Br:8][C:9]1[C:10]([Cl:18])=[CH:12][C:13]([F:17])=[C:14]([CH3:16])[CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10996Butyl nitriteHCID 27733792-Bromo-5-fluoro-4-methylaniline

Product 1

HCID 27732735-Bromo-4-chloro-2-fluorotoluene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
60 °C

Procedure

Cupric chloride (6 g) and butyl nitrite (4.8 g) were added to acetonitrile (16 ml), and the mixture was stirred at 60° C. for 10 minutes. A solution of 2-bromo-5-fluoro-4-methylaniline (7.6 g) in acetonitrile (30 ml) was added dropwise to the mixture at the same temperature, and the resultant mixture was then stirred at the same temperature for 30 minutes. After the reaction mixture was allowed to cool, 2N hydrochloric acid was added to acidify the reaction mixture, and it was extracted with diethyl ether. After an organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off. The residue was subjected to column chromatography on silica gel to conduct elution with n-hexane, thereby obtaining the title compound (5.6 g) as a pale yellow oil.

Workup

  1. temperatureto cool
  2. extractionwas extracted with diethyl ether
  3. dry with materialAfter an organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. washelution with n-hexane

Sources & evidence

ORD record
ord-d21dca6fcecf40589c50774b204a76af
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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