Potassium Carbonate → (4-((2-Methoxyethyl)thio)phenyl)boronic acid

HRID 423528Notes

Reaction equation

HRID 423528 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[CH:4][CH:3]=1.Br[CH2:12][CH2:13][O:14][CH3:15].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:15][O:14][CH2:13][CH2:12][S:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 44318944-Mercaptophenylboronic acid

Product 1

HCID 66672606(4-((2-Methoxyethyl)thio)phenyl)boronic acidYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-mercaptophenylboronic acid (1.0 g, 90%, 5.84 mmol), 1-bromo-2-methoxyethane (1.8 g, 13 mmol) and K2CO3 (2.70 g, 19.5 mmol) in CH3CN (20 mL) was stirred at ambient temperature overnight. After CH3CN was removed, water was added to the residue, and the solid was collected via filtration and washed with water to give 0.9 g of the crude (4-{[2-(methoxy)ethyl]thio}phenyl)boronic acid (75% pure by LC-MS). The crude boronic acid was used without further purification.

Workup

  1. customAfter CH3CN was removed
  2. additionwater was added to the residue
  3. filtrationthe solid was collected via filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-3e40f705db394b5298016163563af8bb
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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