N-bromobutanimide → Methyl 2-amino-5-bromo-3-methoxybenzoate

HRID 249918

Reaction equation

HRID 249918 reaction equation
[NH2:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C1C(=O)N([Br:21])C(=O)C1>CN(C=O)C>[NH2:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([Br:21])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 602320Methyl 2-amino-3-methoxybenzoate

Product 1

HCID 13894022Methyl 2-amino-5-bromo-3-methoxybenzoateYield 73.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 2-amino-3-methoxybenzoate (13.0 g, 71.8 mmol) in DMF (30 mL) was added NBS (14.38 g, 80.8 mmol) at room temperature and the resulting reaction mixture was stirred for 17 h. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by column chromatography (silica gel, 2% to 5% EtOAc in hexanes) to afford methyl 2-amino-5-bromo-3-methoxybenzoate (13.7 g, 73%). 1H NMR consistent.

Workup

  1. customthe resulting reaction mixture
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting residue was purified by column chromatography (silica gel, 2% to 5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d353f3eec5444e8a9d7627517f89b31a
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Linked notes

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