Water → 4-(2-Hydroxy-2-methylpropoxy)-3-methoxyphenylboronic acid

HRID 1044407Notes

Reaction equation

HRID 1044407 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[C:13]([B:15]2[O:19]C(C)(C)C(C)(C)[O:16]2)[CH:12]=[CH:11][C:4]=1[O:5][CH2:6][C:7]([CH3:10])([OH:9])[CH3:8].O.I([O-])(=O)(=O)=O.[Na+].C([O-])(=O)C.[NH4+]>CC(C)=O>[OH:9][C:7]([CH3:10])([CH3:8])[CH2:6][O:5][C:4]1[CH:11]=[CH:12][C:13]([B:15]([OH:16])[OH:19])=[CH:14][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 517165Ammonium AcetateHCID 23667635Sodium periodateHCID 585798871-(2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)-2-methylpropan-2-ol

Product 1

HCID 585798634-(2-Hydroxy-2-methylpropoxy)-3-methoxyphenylboronic acidYield 67.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)-2-methylpropan-2-ol Part B (0.880 g, 2.73 mmol) in acetone (20 mL) and water (20 mL) was added sodium periodate (2.3 g, 10.92 mmol) and ammonium acetate (0.84 g, 10.92 mmol). The mixture stirred at RT overnight. Filtered the white solids, washed the filter cake with acetone and removed the acetone. The product was then extracted with EtOAc, and brine, and, dried (MgSO4), concentrated to afford the crude product. Residue was purified using ISCO flash chromatography (silica gel/methylene chloride-methanol 100:0 to 85:15 gradient) to afford the desired product 4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenylboronic acid 9C (0.443 g, 1.845 mmol, 67.6% yield) as a light brown solid.

Workup

  1. filtrationFiltered the white solids
  2. washwashed the filter cake with acetone
  3. customremoved the acetone
  4. extractionThe product was then extracted with EtOAc, and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customto afford the crude product
  8. customResidue was purified

Sources & evidence

ORD record
ord-2384028f86b64b72829528bd30a2516a
Source dataset
uspto-grants-2013_10
Patent number
US08563583B2

Reaction notes

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