N-bromobutanimide → 2-Amino-5-bromo-3-methoxybenzoic acid

HRID 588807Notes

Reaction equation

HRID 588807 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].C1C(=O)N([Br:20])C(=O)C1>CO>[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([Br:20])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 2557202-Amino-3-methoxybenzoic acid

Product 1

HCID 454804572-Amino-5-bromo-3-methoxybenzoic acidYield 54.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-amino-3-methoxybenzoic acid (5 g, 29.9 mmol) in MeOH (35 mL) at −5° C., NBS (5.59 g, 31.4 mmol) was added and the resulting mixture was stirred at 0° C. for 16 h. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo to afford the crude product (4 g, 54% yield). ESI-MS m/z: 244.2 [M−H]−.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fd6b79dfec2f4dfebc66ee5862533853
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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