Hydrogen Bromide → 3-Bromo-5-(trifluoromethyl)benzoic acid

HRID 2075066Notes

Reaction equation

HRID 2075066 reaction equation
N[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([OH:7])=[O:6].N([O-])=O.[Na+].[BrH:19]>O.[Cu](Br)Br>[Br:19][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 6095563-Amino-5-(trifluoromethyl)benzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 110867883-Bromo-5-(trifluoromethyl)benzoic acidYield 87%

Reagents, catalysts & solvents 2

HCID 24611Copper bromide (CuBr2)CatalystHCID 962WaterSolvent3×

Procedure

To a stirred suspension of 3-amino-5-(trifluoromethyl)benzoic acid (7.90 gm, 38.5 mmol) in a mixture of hydrobromic acid (43% w/v, 100 mL) and water (100 mL) at 0° C. was slowly added a solution of sodium nitrite (7.97 gm, 0.116 mol) in water (50 mL). After 1 hour the inhomogeneous yellow liquid was added to a solution of copper (II) bromide (16.44 gm, 0.115 mol) in water (100 mL) and the mixture was stirred at room temperature for 16 hours. The mixture was extracted with diethyl ether (250 mL), the aqueous layer was separated and extracted with diethyl ether (3×75 mL). The combined organic layers were dried with anhydrous sodium sulfate and the solvent removed under vacuum to give the title compound as a yellow solid (9.0 gm, 87%) which was used in the following reaction without further purification.

Workup

  1. extractionThe mixture was extracted with diethyl ether (250 mL)
  2. customthe aqueous layer was separated
  3. extractionextracted with diethyl ether (3×75 mL)
  4. dry with materialThe combined organic layers were dried with anhydrous sodium sulfate
  5. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-294ed456af02454ca053e28bf8a466ce
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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