Hydrochloric Acid → HCID 22171331, compound

HRID 30745Notes

Reaction equation

HRID 30745 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 min. 2 mol/L hydrochloric acid (0.082 mL) was added, 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 min
  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-5c7ec42c01ef402fb8b68fbfd3b86c6a
Source dataset
uspto-grants-2008_09
Patent number
US07423185B2

Reaction notes

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