Acetic Acid → Methyl Benzoate

HRID 1530237Notes

Reaction equation

HRID 1530237 reaction equation
N[C:2]1[C:3](C)=[C:4]([CH:9]=[C:10](Br)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C1(=O)CCCC1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:9]=[CH:10][CH:11]=[CH:2][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8452CyclopentanoneHCID 5003444Sodium cyanoborohydrideHCID 24729181Methyl 3-Amino-5-bromo-2-methylbenzoate

Product 1

HCID 7150Methyl BenzoateYield 142.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 3-amino-5-bromo-2-methylbenzoate (5 g, 20.57 mmol) and cyclopentanone (8.64 g, 102.8 mmol) in methanol (30 mL), acetic acid (2.46 g, 41.1 mmol) was added and reaction stirred at room temperature for 3 h. Then sodium cyanoborohydride (3.23 g, 51.4 mmol) was added and reaction stirred overnight. On completion, solvent was removed under reduced pressure and crude material was purified by column chromatography to afford methyl 5-bromo-3-(cyclopentylamino)-2-(methylbenzoate (4 g, 78.2%).

Workup

  1. customreaction
  2. customreaction
  3. stirringstirred overnight
  4. customOn completion, solvent was removed under reduced pressure and crude material
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-8721007e08ef4d1ba2b4dae8e175f00a
Source dataset
uspto-grants-2015_07
Patent number
US09090562B2

Reaction notes

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