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

HRID 495978Notes

Reaction equation

HRID 495978 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-f07fb661d1c948f5b826c1d25a498af8
Source dataset
uspto-grants-2005_09
Patent number
US06943169B2

Reaction notes

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