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

HRID 2079623

Reaction equation

HRID 2079623 reaction equation
[NH2:1][C:2]1[C:10]([F: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]([F: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 5864082-Amino-3-fluorobenzoic acid

Product 1

HCID 404245972-Amino-5-bromo-3-fluorobenzoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a suspension of 2-amino-3-fluorobenzoic acid (5 g, 32.2 mmol) in chloroform (200 mL) was added dropwise bromine (1.1 equiv.) in chloroform (125 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 9.6 g of white powder as HBr salt of 2-amino-5-bromo-3-fluorobenzoic acid (95% yield). ES/MS m/z 234/236 (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-465e8168695f4c588921e7bc7792097b
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Linked notes

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