Methanol → Methyl 2-amino-5-bromobenzoate

HRID 511292Notes

Reaction equation

HRID 511292 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].OS(O)(=O)=O.[CH3:17]O>>[CH3:17][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([Br:11])[CH:9]=[CH:10][C:2]=1[NH2:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 798582-Amino-5-bromobenzoic acid

Product 1

HCID 736224Methyl 2-amino-5-bromobenzoateYield 76%

Procedure

2-Amino-5-bromobenzoic acid (80 g, 0.37 mmol) was dissolved in MeOH (600 mL) and a solution of H2SO4 (50 mL) was slowly added. The reaction mixture was refluxed for 72 h, then concentrated. NaOH solution was added to adjust the pH to 10-11. The mixture was extracted with EtOAc (3×500 mL). The combined organic layer was dried over MgSO4, concentrated to afford the desired compound (65 g, yield: 76%) as a colorless oil, which is used directly in the next step without purification.

Workup

  1. temperatureThe reaction mixture was refluxed for 72 h
  2. concentrationconcentrated
  3. additionNaOH solution was added
  4. extractionThe mixture was extracted with EtOAc (3×500 mL)
  5. dry with materialThe combined organic layer was dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e94b30176982426ca5bff079e2580af4
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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