Hydrochloric Acid → 2-BROMO-1-CHLORO-4-(TRIFLUOROMETHOXY)BENZENE

HRID 1267893Notes

Reaction equation

HRID 1267893 reaction equation
N(OC(C)(C)C)=O.[Br:8][C:9]1[CH:15]=[C:14]([O:16][C:17]([F:20])([F:19])[F:18])[CH:13]=[CH:12][C:10]=1N.[ClH:21]>C(#N)C.[Cu](Cl)Cl>[Br:8][C:9]1[CH:15]=[C:14]([O:16][C:17]([F:20])([F:19])[F:18])[CH:13]=[CH:12][C:10]=1[Cl:21]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 6882962-Bromo-4-(trifluoromethoxy)aniline

Product 1

HCID 27614052-BROMO-1-CHLORO-4-(TRIFLUOROMETHOXY)BENZENE

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6342AcetonitrileSolvent2×

Procedure

To anhydrous copper(II)chloride (6.3 g, 47 mmol) in acetonitrile (100 mL) was added tert-butyl nitrite (6.85 mL, 58 mmol), followed dropwise by a solution of 2-bromo-4-(trifluoromethoxy)aniline (10 g, 39 mmol) in acetonitrile (15 mL). The solution was stirred at ambient temperature for 1 hour then poured into hydrochloric acid (250 mL, 2M). The suspension formed was extracted with diethyl ether (2×250 mL) and the extracts were dried (MgSO4). Concentration yielded the title compound as an oil (7.82 g, 28 mmol).

Workup

  1. customThe suspension formed
  2. extractionwas extracted with diethyl ether (2×250 mL)
  3. dry with materialthe extracts were dried (MgSO4)
  4. concentrationConcentration

Sources & evidence

ORD record
ord-0e1df7a490df45c087f1eafb4a26fd4f
Source dataset
uspto-grants-2003_04
Patent number
US06555552B2

Reaction notes

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