Bromine → Methyl 4-amino-3-bromo-5-methoxybenzoate

HRID 1453642Notes

Reaction equation

HRID 1453642 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[NH2:13])[C:6]([O:8][CH3:9])=[O:7].[Br:14]Br>CO.C(O)(=O)C>[Br:14][C:11]1[CH:10]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:12]=1[NH2:13])[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 2

HCID 24408BromineHCID 602411Methyl 4-amino-3-methoxybenzoate

Product 1

HCID 22324265Methyl 4-amino-3-bromo-5-methoxybenzoateYield 115.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

10.5 Grams (55 mmole) of methyl 3-methoxy-4-aminobenzoate was dissolved in 80 ml methanol, and 3.0 ml bromine (55 mmole) in 20 ml acetic acid was added dropwise at room temperature. The solution was stirred for three hours at room temperature and the solvents were evaporated under reduced pressure. The residue was treated with sodium bicarbonate solution and the product was filtered and air-dried to yield 16.5 grams of methyl 3-bromo-5-methoxy-4-aminobenzoate.

Workup

  1. customthe solvents were evaporated under reduced pressure
  2. additionThe residue was treated with sodium bicarbonate solution
  3. filtrationthe product was filtered
  4. customair-dried

Sources & evidence

ORD record
ord-c11664d8f7cb4ddba126ea6c5a62ae0a
Source dataset
uspto-grants-2009_01
Patent number
US07476675B2

Reaction notes

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