Hydrochloric Acid → 4-Bromo-1-chloro-2-(trifluoromethoxy)benzene

HRID 2356007Notes

Reaction equation

HRID 2356007 reaction equation
N(OC(C)(C)C)=O.[Br:8][C:9]1[CH:15]=[CH:14][C:12](N)=[C:11]([O:16][C:17]([F:20])([F:19])[F:18])[CH:10]=1.[ClH:21]>C(#N)C.[Cu](Cl)Cl>[Br:8][C:9]1[CH:15]=[CH:14][C:12]([Cl:21])=[C:11]([O:16][C:17]([F:20])([F:19])[F:18])[CH:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 7373824-Bromo-2-(trifluoromethoxy)aniline

Product 1

HCID 227302024-Bromo-1-chloro-2-(trifluoromethoxy)benzene

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of tert-butyl nitrite (1.78 mL, 15.0 mmol), copper (II) chloride (1.61 g, 12.0 mmol) and 4-bromo-2-(trifluoromethoxy)aniline (2.56 g, 10.0 mmol) in acetonitrile (40 mL) was heated to 70° C., stirred for 3 hours, cooled to room temperature, poured into 0.5M HCl, and extracted with diethyl ether. The combined extracts were washed with water and brine, dried (MgSO4), filtered, and concentrated to provide the desired product. MS (ESI(+)) m/e 275 (M+H)+.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with diethyl ether
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8bf5ece002124a2fbadcfde6e698e8d7
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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