Water → Methyl 2-amino-5-bromo-3-methoxybenzoate

HRID 576327

Reaction equation

HRID 576327 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].[Br:14]N1C(=O)CCC1=O.O>CN(C=O)C>[NH2:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([Br:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 602320Methyl 2-amino-3-methoxybenzoate

Product 1

HCID 13894022Methyl 2-amino-5-bromo-3-methoxybenzoateYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of compound 53 (22.4 g, 123 mmol) in DMF (250 mL) was added N-bromosuccinimide (21.9 g, 123 mmol) portionwise at 0° C. The mixture was stirred at 0° C. for 0.5 h. To the mixture was added water and extracted with EtOAc (500 mL×2). The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the desired compound 54 (27.5 g, 86%) as a white solid.

Workup

  1. extractionextracted with EtOAc (500 mL×2)
  2. dry with materialThe combined organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dd0c574c13a842c8a23be71b3f6275b0
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Linked notes

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