Hydrogen Bromide → 1-Bromo-2-chloro-4-(trifluoromethoxy)benzene

HRID 342977Notes

Reaction equation

HRID 342977 reaction equation
N([O-])=O.[Na+].[Cl:5][C:6]1[CH:12]=[C:11]([O:13][C:14]([F:17])([F:16])[F:15])[CH:10]=[CH:9][C:7]=1N.[BrH:18]>S(=O)(=O)(O)O.C(O)(=O)C.O>[Cl:5][C:6]1[CH:12]=[C:11]([O:13][C:14]([F:17])([F:16])[F:15])[CH:10]=[CH:9][C:7]=1[Br:18]

Participants

7

Reactant 3

HCID 260Hydrogen BromideHCID 27340842-Chloro-4-(trifluoromethoxy)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 534140341-Bromo-2-chloro-4-(trifluoromethoxy)benzene

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of sodium nitrite (16.31 g) in concentrated sulphuric acid was added dropwise to a solution of 2-chloro-4-trifluoromethoxyaniline (50 g) in acetic acid, while maintaining the temperature below 10° C. The mixture was stirred at 5°-10° C. for 0.5 hours then added slowly to a mixture of cuprous bromide (33.9 g) in aqueous hydrobromic acid (200 ml) and ice. The mixture was stirred at room temperature for 0.5 hours and left to stand overnight. The mixture was diluted with water and extracted with dichloromethane, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give 2-chloro-4-trifluoromethoxybromobenzene (63.64 g) as a brown oil which was not further purified.

Workup

  1. temperaturewhile maintaining the temperature below 10° C
  2. stirringThe mixture was stirred at room temperature for 0.5 hours
  3. waitleft
  4. waitto stand overnight
  5. extractionextracted with dichloromethane
  6. washwashed with water
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-be70d093f5cd4d11af9348bb3408e6fd
Source dataset
uspto-grants-1999_01
Patent number
US05859283

Reaction notes

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