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

HRID 1866150Notes

Reaction equation

HRID 1866150 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-e1441b7bdd674c9cb58941a16959c326
Source dataset
uspto-grants-2009_12
Patent number
US07629366B2

Reaction notes

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