Hydrochloric Acid → 6-Bromo-3-chloro-2-fluorobenzotrifluoride

HRID 341738

Reaction equation

HRID 341738 reaction equation
N([O-])=O.[Na+].[Br:5][C:6]1[CH:12]=[CH:11][C:9](N)=[C:8]([F:13])[C:7]=1[C:14]([F:17])([F:16])[F:15].[ClH:18]>S(=O)(=O)(O)O.C(O)(=O)C.O.[Cu]Cl>[Br:5][C:6]1[C:7]([C:14]([F:17])([F:16])[F:15])=[C:8]([F:13])[C:9]([Cl:18])=[CH:11][CH:12]=1

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 536697144-Bromo-2-fluoro-3-(trifluoromethyl)aniline

Product 1

HCID 536324436-Bromo-3-chloro-2-fluorobenzotrifluoride

Reagents, catalysts & solvents 4

HCID 62652Cuprous chlorideCatalystHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of sodium nitrite (7.3 g) in concentrated sulphuric acid was added to a stirred cooled solution of 4-bromo-2-fluoro-3-trifluoromethylaniline (27.4 g) in glacial acetic acid while maintaining the temperature below 15° C. The mixture was stirred at 10°-15° C. for one and a half hours then poured into a mixture of copper (I) chloride (10.5 g) in hydrochloric acid (5M). The mixture was stirred for one and a half hours then diluted with water, extracted with ether, washed with aqueous sodium hydroxide solution (2M), water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was distilled to give 6-bromo-3-chloro-2-fluorobenzotrifluoride (8.3 g) as a yellow oil b.p. 44°-45° C./2 mbar.

Workup

  1. temperaturewhile maintaining the temperature below 15° C
  2. stirringThe mixture was stirred for one and a half hours
  3. extractionextracted with ether
  4. washwashed with aqueous sodium hydroxide solution (2M), water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. distillationthe residue was distilled

Sources & evidence

ORD record
ord-fdf4db2069834267a19313abb8d6b659
Source dataset
uspto-grants-1999_01
Patent number
US05856274

Linked notes

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