Bromine → Hydrogen Bromide

HRID 2079632Notes

Reaction equation

HRID 2079632 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:12]Br>C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:10]([Br:12])=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[BrH:12]

Participants

5

Reactant 2

HCID 24408Bromine2×HCID 1014122-Amino-5-fluorobenzoic acid

Product 2

HCID 260Hydrogen BromideHCID 27817032-Amino-3-bromo-5-fluorobenzoic acid

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To 2-Amino-5-fluorobenzoic acid (5 g, 32.2 mmol) in chloroform (90 mL) was added bromine (1.82 mL, 35.4 mmol) in chloroform (10 mL) solution dropwise via an additional funnel. The mixture was stirred at room temperature for 16 hrs. and LC/MS showed about 50% conversion of the starting material. Additional bromine (1.8 mL) was added to the reaction and continued stirring for another 24 hrs. The resulting white precipitate was collected by filtration, washed thoroughly with dichloromethane and air-dried to give 2-amino-3-bromo-5-fluorobenzoic acid as its HBr salt. ES/MS m/z 234/236 (MH+).

Workup

  1. stirringcontinued stirring for another 24 hrs
  2. filtrationThe resulting white precipitate was collected by filtration
  3. washwashed thoroughly with dichloromethane
  4. customair-dried

Sources & evidence

ORD record
ord-f2c2bc12c9f04b6880c938bc0b5ad131
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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