Water → 4-Amino-3-bromo-5-(trifluoromethoxy)benzoic acid

HRID 2216768Notes

Reaction equation

HRID 2216768 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:11][C:12]([F:15])([F:14])[F:13].[Br:16]Br.O>C(O)(=O)C>[NH2:1][C:2]1[C:3]([O:11][C:12]([F:13])([F:14])[F:15])=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:9][C:10]=1[Br:16]

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 27359514-amino-3-(trifluoromethoxy)benzoic Acid

Product 1

HCID 219424074-Amino-3-bromo-5-(trifluoromethoxy)benzoic acidYield 57.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 4-amino-3-trifluoromethoxybenzoic acid (5 g, 22.6 mmoles) in acetic acid (50 mL), bromine (3.98 g, 24.9 mmoles) in acetic acid (10 mL) was added dropwise at room temperature. After the reaction mixture was kept stirring for one hour, water was added into the mixture. The solid was filtered and washed with water to give 4-amino-3-bromo-5-trifluoromethoxybenzoic acid (3.9 g, 54.9%).

Workup

  1. filtrationThe solid was filtered
  2. washwashed with water

Sources & evidence

ORD record
ord-4a116d547ab140c49ab55dfcb9149b51
Source dataset
uspto-grants-2006_09
Patent number
US07112595B2

Reaction notes

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