Ammonium Acetate → 3-Methoxy-4-(methoxycarbonyl)benzeneboronic acid

HRID 1823090Notes

Reaction equation

HRID 1823090 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([B:13]2[O:17]C(C)(C)C(C)(C)[O:14]2)[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].C([O-])(=O)C.[NH4+].I([O-])(=O)(=O)=O.[Na+]>CC(C)=O.O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([B:13]([OH:14])[OH:17])[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 22171502Methyl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoateHCID 23667635Sodium periodate

Product 1

HCID 177502563-Methoxy-4-(methoxycarbonyl)benzeneboronic acidYield 97.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a suspension of methyl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (2.0 g) in acetone (70 ml) and water (70 ml) was added ammonium acetate (1.11 g) and sodium periodate (3.08 g), and the mixture was stirred at room temperature for 15 hours. The solvent was evaporated and the residue was diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure to give [3-methoxy-4-(methoxycarbonyl)phenyl]-boronic acid (1.4 g).

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was diluted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-31e803cde36d41a288b0c5e46dc81865
Source dataset
uspto-grants-2006_05
Patent number
US07037938B2

Reaction notes

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