Bromine → 2-Amino-5-bromo-3-methoxybenzoic acid

HRID 2079612Notes

Reaction equation

HRID 2079612 reaction equation
[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:13]Br>C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([Br:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 24408BromineHCID 2557202-Amino-3-methoxybenzoic acid

Product 1

HCID 454804572-Amino-5-bromo-3-methoxybenzoic acidYield 99%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a 0.24 M chloroform solution of 2-amino-3-methoxybenzoic acid (4, 11.87 g, 71.7 mmol) at 0° C. was added bromine (1.08 eq. 0.31 M) in chloroform dropwise. The mixture was warmed to room temperature and stirred under argon for 16 hours. The resulting precipitate was collected by filtration and washed thoroughly with chloroform. The crude material was dried in vacuo to give the title as an HBr salt in 99% yield. ES/MS m/z 248/250 (MH+).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed thoroughly with chloroform
  3. dry with materialThe crude material was dried in vacuo

Sources & evidence

ORD record
ord-24ee5bcf2bf34b0fbb9374fe09749cd6
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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