Hydrogen Bromide → 3-Bromo-4-(trifluoromethoxy)benzoic acid

HRID 1678524Notes

Reaction equation

HRID 1678524 reaction equation
N[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][C:12]([F:15])([F:14])[F:13])[C:5]([OH:7])=[O:6].N([O-])=O.[Na+].[BrH:20]>O.[Cu]Br>[Br:20][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][C:12]([F:15])([F:14])[F:13])[C:5]([OH:7])=[O:6]

Participants

6

Reactant 3

HCID 260Hydrogen Bromide2×HCID 202740943-Amino-4-(trifluoromethoxy)benzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 202740913-Bromo-4-(trifluoromethoxy)benzoic acid

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 962WaterSolvent3×

Procedure

To a stirred solution of 3-amino-4-trifluoromethoxybenzoic acid (2 g) in a mixture of water (16 ml) and 48% HBr (12 ml) at 0° C. was added a solution of sodium nitrite (0.64 g) in water (8 ml) drop-wise. After 15 min at 0° C. the reaction mixture was diluted with water (12 ml) and carefully poured onto a stirred solution of copper (I) bromide (1.32 g) in 48% HBr (8 ml) at room temperature. The resulting suspension was filtered, and the residue washed with water (3×5 ml) and dried in vacuo to give the title compound as a beige solid (2.08 g).

Workup

  1. filtrationThe resulting suspension was filtered
  2. washthe residue washed with water (3×5 ml)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-af4ca4b19ca64f8880d3e503a2751bde
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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