Hydrochloric Acid → HCID 22171331, compound

HRID 2220619Notes

Reaction equation

HRID 2220619 reaction equation
I([O-])(=O)(=O)=O.[Na+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=1[B:20]1[O:24]C(C)(C)C(C)(C)[O:21]1)[C:12]([O:14][CH2:15][CH3:16])=[O:13].Cl>C(OCC)(=O)C.O.O1CCCC1>[CH2:15]([O:14][C:12]([C:11]1[CH:17]=[CH:18][C:19]([B:20]([OH:21])[OH:24])=[C:9]([O:8][CH3:7])[CH:10]=1)=[O:13])[CH3:16]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 22171560Ethyl 3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoateHCID 23667635Sodium periodate

Product 1

HCID 22171331HCID 22171331, compoundYield 89.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium metaperiodate (0.157 g) was added to a mixture of ethyl 3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (0.075 g), water (1 mL) and tetrahydrofuran (4 mL) at room temperature with stirring, and the mixture was stirred at that temperature for 10 minutes. To the mixture was added 2 mol/L hydrochloric acid (0.082 mL), and the resulting mixture was stirred at that temperature for additional 2 hrs, then water and ethyl acetate were added. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to afford 4-ethoxycarbonyl-2-methoxyphenylboronic acid (0.049 g).

Workup

  1. stirringthe mixture was stirred at that temperature for 10 minutes
  2. stirringthe resulting mixture was stirred at that temperature for additional 2 hrs
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-fb24d5f6a93d4248bd697c1268bde1f0
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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