Hydrogen Bromide → 2-Amino-5-bromo-3-chlorobenzoic acid

HRID 2079625

Reaction equation

HRID 2079625 reaction equation
[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:12]Br.Br>C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:8]([Br:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24408BromineHCID 808072-Amino-3-chlorobenzoic acid

Product 1

HCID 8279792-Amino-5-bromo-3-chlorobenzoic acidYield 87%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a suspension of 2-amino-3-chlorobenzoic acid (2 g, 11.6 mmol) in chloroform (120 mL) was added dropwise bromine (1.1 equiv.) in chloroform (12 mL) solution. The mixture was stirred at room temperature for 16 hrs. The resulting white solid was collected by filtration and washed thoroughly with methylene chloride until the filtrate was colorless. The solid was air-dried to give 3.35 g of white powder as HBr salt of 2-amino-5-bromo-3-chlorobenzoic acid (87% yield). ES/MS m/z 250/252 (MH+).

Workup

  1. filtrationThe resulting white solid was collected by filtration
  2. washwashed thoroughly with methylene chloride until the filtrate
  3. customThe solid was air-dried

Sources & evidence

ORD record
ord-3f417d96222c474b91be7cd3eaffa9f3
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Linked notes

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