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

HRID 2059848Notes

Reaction equation

HRID 2059848 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 C (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 4D (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-18e3aeaed0be41b6a4c735930c3a6664
Source dataset
uspto-grants-2012_10
Patent number
US08278316B2

Reaction notes

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